Herbicide compositions

ABSTRACT

Herbicidal compositions consisting of an active herbicidal compound and an antidote therefor and the methods of use of the herbicide composition are described herein. The antidote compound corresponds to the formula: ##STR1## wherein R can be selected from the group consisting of haloalkyl; haloalkenyl; alkyl; alkenyl; cycloalkyl; cycloalkylalkyl; halogen; hydrogen; carboalkoxy; N-alkenylcarbamylalkyl; N-alkenylcarbamyl; N-alkyl-N-alkynylcarbamyl; N-alkyl-N-alkynylcarbamylalkyl; N-alkenylcarbamylalkoxyalkyl; N-alkyl-N-alkynylcarbamylalkoxyalkyl; alkynoxy; haloalkoxy; thiocyanatoalkyl; alkenylaminoalkyl; alkylcarboalkyl; cyanoalkyl; cyanatoalkyl; alkneylaminosulfonoalkyl; alkylthioalkyl; haloalkylcarbonyloxyalkyl; alkyoxycarboalkyl; haloalkenylcarbonyloxyalkyl; hydroxyhaloalkyloxyalkyl; hydroxyalkylcarboalkyoxyalkyl; hydroxyalkyl; alkoysulfonoalkyl; furyl; thienyl; alkyldithiolenyl; thienalkyl; phenyl and substituted phenyl wherein said substituents can be selected from halogen, alkyl, haloalkyl, alkoxy, carbamyl, nitro, carboxylic acids and their salts, haloalkylcarbamyl; phenylalkyl; phenylhaloalkyl; phenylalkenyl; substituted phenylalkenyl wherein said substitutents can be selected from halogen, alkyl, alkoxy; halophenoxy; phenylalkoxy; phenylalkylcarboxyalkyl; phenylcycloalkyl; halophenylalkenoxy; halothiophenylalkyl; halophenoxyalkyl; bicycloalkyl; alkenylcarbamylpyridinyl; alkynylcarbamylpyridinyl; dialkenylcarbamylbicycloalkenyl; alkynylcarbamylbicycloalkenyl; R 1  and R 2  can be the same or different and can be selected from the group consisting of alkenyl; haloalkenyl; hydrogen; alkyl; haloalkyl; alkynyl; cyanoalkyl; hydroxyalkyl; hydroxyhaloalkyl; haloalkylcarboxyalkyl; alkylcarboxyalkyl; alkoxycarboxyalkyl; thioalkylcarboxyalkyl; alkoxycarboalkyl; alkylcarbamyloxyalkyl; amino; formyl; haloalkyl-N-alkylamido; haloalkylamido; haloalkylamidoalkyl; haloalkyl-N-alkylamidoalkyl; haloalkylamidoalkenyl; alkylimino; cycloalkyl; alkylcycloalkyl; alkoxyalkyl; alkylsulfonyloxyalkyl; mercaptoalkyl; alkylaminoalkyl; alkyoxycarboalkenyl; haloalkylcarbonyl; alkylcarbonyl; alkenylcarbamyloxyalkyl; cycloalkylcarbamyloxyalkyl; alkoxycarbonyl; haloalkoxycarbonyl; halophenylcarbamyloxyalkyl; cycloalkenyl; phenyl; substituted phenyl wherein said substituents can be selected from alkyl, halogen, haloalkyl, alkoxy, haloalkylamido, phthalamido, hydroxy, alkylcarbamyloxy, alkenylcarbamyloxy, alkylamido, haloalkylamido, alkylcarboalkenyl; phenylsulfonyl; phenylalkyl; substituted phenylalkyl wherein said substitutents can be selected from halogen, alkyl, dioxyalkylene, halophenoxyalkylamidoalkyl; alkylthiodiazolyl; piperidylalkyl; thiazolyl; alkylthiazolyl; benzothiazolyl; halobenzothiazolyl; furylalkyl; pyridyl; alkylpyridyl; alkyloxazolyl; tetrahydrofurylalkyl; 3-cyano, 4,5-polyalkylene-thienyl; α-haolalkylacetamidophenylalkyl; α-haloalkylacetamidonitrophenylalkyl; α-haloalkylacetamidohalophenylalkyl; cyanoalkenyl; R 1  and R 2  when taken together can form a structure consisting of piperidinyl; alkylpiperidinyl; alkyltetrahydropyridyl; morpholyl; alkylmorpholyl; azo-bicyclononyl; benzoalkylpyrrolidinyl; oxazolidyl; alkyloxazolidyl; perhydroquinolyl; alkylaminoalkenyl; provided that when R 1  is hydrogen R 2  is other than hydrogen and halophenyl.

CROSS REFERENCE TO RELATED APPLICATION

This application is a continuation of Ser. No. 06/480,185, filed Mar.28, 1983, abandoned which is a division of Ser. No. 06/369,322, filedApr. 16, 1982, now U.S. Pat. No. 4,415,352, which is a division of Ser.No. 06/196,517, filed Oct. 14, 1980, abandoned which is a division ofSer. No. 05/930,967, filed Aug. 4, 1978, now U.S. Pat. No. 4,269,618,granted May 26, 1981, which is a division of Ser. No. 05/208,041, filedDec. 9, 1971, now U.S. Pat. No. 4,137,070, granted Jan. 30, 1979, whichis a continuation-in part of Ser. No. 05/134,868, filed Apr. 16, 1971,abandoned.

BACKGROUND OF THE INVENTION

Among the many herbicidal compounds commercially available thethiolcarbamates alone or admixed with other herbicides, such as thetriazines, have reached a relatively high degree of commercial success.These herbicides are immediately toxic to a large number of weed pestsat different concentrations varying with the resistance of the weedpests. Some examples of these compounds are described and claimed in theU.S. Pat. Nos. 2,913,327, 3,037,853, 3,175,897, 3,185,720, 3,198,786 and3,582,314. It has been found in practice that the use of thesethiolcarbamates as herbicides on crops sometimes causes serious injuriesto the crop plant. When used in the recommended amounts in the soil tocontrol many broadleaf weeds and grasses, serious malformation andstunting of the crop plants result. This abnormal growth in the cropplants results in loss of crop yield. Previous attempts to overcome thisproblem involves the treatment of the crop seed with certainantagonistic agents prior to planting, see U.S. Pat. No. 3,131,509.These antagonistic agents have not been notably successful.

DESCRIPTION OF THE INVENTION

It has been discovered that plants can be protected against injury bythe thiolcarbamates alone or mixed with other compounds and/or thetolerance of the plants can be substantially increased to the activecompounds of the above-noted U.S. Patents by adding to the soil anantidote compound corresponding to the following formula: ##STR2##wherein R can be selected from the group consisting of haloalkyl;haloalkenyl; alkyl; alkenyl; cycloalkyl; cycloalkylalkyl; halogen;hydrogen; carboalkoxy; N-alkenylcarbamylalkyl; N-alkenylcarbamyl;N-alkyl-N-alkynylcarbamyl; N-alkyl-N-alkynylcarbamylalkyl;N-alkenylcarbamylalkoxyalkyl; N-akyl-N-alkynylcarbamylalkoxyalkyl;alkynoxy; haloalkoxy; thiocyanatoalkyl; alkenylaminoalkyl;alkylcarboalkyl; cyanoalkyl; cyanatoalkyl; alkenylaminosulfonoalkyl;alkylthioalkyl; haloalkylcarbonyloxyalkyl; alkyoxycarboalkyl;haloalkenylcarbonyloxyalkyl; hydroxyhaloalkyloxyalkyl;hydroxyalkylcarboalkyoxyalkyl; hydroxyalkyl; alkoxysulfonoalkyl; furyl,thienyl; alkyldithiolenyl; thienalkyl; phenyl and substituted phenylwherein said substituents can be selected from halogen, alkyl,haloalkyl, alkoxy, carbamyl, nitro, carboxylic acids and their salts,haloalkylcarbamyl; phenylalkyl; phenylhaloalkyl; phenylalkenyl;substituted phenylalkenyl wherein said substituents can be selected fromhalogen, alkyl, alkoxy; halophenoxy; phenylalkoxy;phenylalkylcarboxyalkyl; phenylcycloalkyl; halophenylalkenoxy;halothiophenylalkyl; halophenoxyalkyl; bicycloalkyl;alkenylcarbamylpyridinyl; alkynylcarbamylpyridinyl;dialkenylcarbamylbicycloalkenyl; alkynylcarbamylbicycloalkenyl; R₁ andR₂ can be the same or different and can be selected from the groupconsisting of alkenyl; haloalkenyl; hydrogen; alkyl; haloalkyl; alkynyl;cyanoalkyl; hydroxyalkyl; hydroxyhaloalkyl; haloalkylcarboxyalkyl;alkylcarboxyalkyl; alkoxycarboxyalkyl; thioalkylcarboxyalkyl;alkoxycarboalkyl; alkylcarbamyloxyalkyl; amino; formyl;haloalkyl-N-alkylamido; haloalkylamido; haloalkylamidoalkyl;haloalkyl-N-alkylamidoalkyl; haloalkylamidoalkenyl; alkylimino;cycloalkyl; alkylcycloalkyl; alkoxyalkyl; alkylsulfonyloxyalkyl;mercaptoalkyl; alkylaminoalkyl; alkoxycarboalkenyl; haloalkylcarbonyl;alkylcarbonyl; alkenylcarbamyloxyalkyl; cycloalkylcarbamyloxyalkyl;alkoxycarbonyl; haloalkoxycarbonyl; halophenylcarbamyloxyalkyl;cycloalkenyl; phenyl; substituted phenyl wherein said substituents canbe selected from alkyl, halogen, haloalkyl, alkoxy, haloalkylamido,phthalamido, hydroxy, alkylcarbamyloxy, alkenylcarbamyloxy, alkylamido,haloalkylamido, alkylcarboalkenyl; phenylsulfonyl; phenylalkyl;substituted phenylalkyl wherein said substituents can be selected fromhalogen, alkyl; dioxyalkylene, halophenoxyalkylamidoalkyl;alkylthiodiazolyl; piperidylalkyl; thiazolyl; alkylthiazolyl;benzothiazolyl; halobenzothiazolyl; furylalkyl; pyridyl; alkylpyridyl;alkyloxazolyl; tetrahydrofurylalkyl; 3-cyano, 4,5-polyalkylene-thienyl;α-haloalkylacetamidophenylalkyl; α-haloalkylacetamidonitrophenylalkyl;α-haloalkylacetamidohalophenylalkyl; cyanoalkenyl; R₁ and R₂ when takentogether can form a structure consisting of piperidinyl;alkylpiperidinyl; alkyltetrahydropyridyl; morpholyl; alkylmorpholyl;azobicyclononyl; benzoalkylpyrrolidinyl; oxazolidyl; alkyloxazolidyl;perhydroquinolyl; alkylaminoalkenyl; provided that when R₁ is hydrogenR₂ is other than hydrogen and halophenyl.

The compounds represented by the above formula can be synthesized bymixing together an appropriate acid chloride with an appropriate amine.A solvent such as benzene can be used if desired. The reaction ispreferably carried out at reduced temperatures. After the reaction iscomplete, the end-product is brought to room temperature and can bereadily separated.

In order to illustrate the merits of the present invention, reference ismade to the following examples:

EXAMPLE 1 ##STR3##

A solution was made by dissolving 3.7 g. (0.025 mole) of dichloroacetylchloride in 100 ml. of methylene dichloride which was then cooled toabout 5° C. in an ice bath. Then, 4.9 g. (0.05 mole) of diallyl aminewas added dropwise while the temperature was maintained at below about10° C. The mixture was then stirred at room temperature for about 4hours and washed twice with water and dried over magnesium sulfate,filtered and stripped. The yield was 4.0 g., n_(D) ³⁰ -1.4990.

EXAMPLE 2 ##STR4##

A solution was made by dissolving 3.7 g. (0.025 mole) of dichloroacetylchloride in 100 ml. of methylene dichloride which was then cooled toabout 10° C. in an ice bath. Then, 5.1 g. (0.05 mole) ofdi-n-propylamine was added dropwise while the temperature was maintainedat below about 10° C. The mixture was then stirred at room temperatureovernight and washed twice with water and dried over magnesium sulfate,filtered and stripped. The yield was 3.6 g., n_(D) ³⁰ -1.4778.

EXAMPLE 3 ##STR5##

A solution was made by dissolving 3.7 g (0.025 mole) of dichloroacetylchloride in 80 ml. of methylene dichloride which was then cooled toabout 10° C. in an ice bath. Then, 4.2 g. (0.05 mole) of N-methyl,N-1-methyl-3-propynylamine in 20 ml. of methylene dichloride was addeddropwise while the temperature was maintained about 10° C. The mixturewas then stirred at room temperature for about 4 hours and washed twicewith water and dried over magnesium sulfate, filtered and stripped. Theyield was 2.9 g., n_(D) ³⁰ -1.4980.

EXAMPLE 4 ##STR6##

A solution was formed containing 100 ml. acetone, 5.05 g. furfuryl amine(0.1 mole), then stirred with the addition of 7 ml. triethylamine at 15°C. Then, 5.7 g. of monochloro acetyl chloride was added and stirred for15 more minutes, wherein 500 ml. of water was added. The reaction masswas filtered, washed with dilute hydrochloric acid in additional water,and then dried to constant weight.

EXAMPLE 5 ##STR7##

A solution was formed consisting of 5.7 g. (0.05 mole) of amino methylthiazole in 100 ml. of benzene with 7 ml. of triethylamine. Thissolution was stirred at 10°-15° C. and then 5.2 ml. (0.05 mole) ofdichloro acetyl chloride was added dropwise. The reaction was stirred atroom temperature for 10 minutes. Then, 100 ml. water was added and thesolution was then washed with benzene solution, dried over magnesiumsulfate and then filtered to remove the solvent.

EXAMPLE 6 ##STR8##

A solution was formed containing 200 ml. acetone and 17.5 g. (0.05 mole)of 2-amino-6-bromo benzothiazole and 7 ml. of triethylamine. Thesolution was stirred 15° C. with cooling. Then 5.2 ml. (0.05 mole) ofdichloroacetyl chloride was added slowly. This solution was stirred atroom temperature for ten minutes. The solid form was filtered off, whichsolid was washed with ether, then cold water, and then filtered againand dried at 40°-50° C.

EXAMPLE 7 ##STR9##

3.4 g. of 3-methyl-3-butynyl amine was dissolved in 50 ml. of methylenechloride, 4.5 g. of triethylamine was added and 7.6 g. of decanoylchloride was added dropwise with stirring and cooling in a water bath.When the reaction was complete the mixture washed with water, dried andthe solvent stripped off to give 7.1 g. of product.

EXAMPLE 8 ##STR10##

A solution was formed containing 5.9 g. of diallyl amine dissolved in 15ml. of methylene chloride and 6.5 g. of triethylamine. Then, 6.3 g. ofcyclopropane carbonyl chloride was added dropwise with stirring andcooling in a water bath. When the reaction was complete the mixture waswashed with water, dried and the solvent stripped off to give 8.2 g. ofproduct.

EXAMPLE 9 ##STR11##

A solution was formed containing 4.5 g. of diallyl amine dissolved in 15ml. of methylene chloride and 5.0 g. of triethylamine. Then, 7.1 g. ofortho-fluorobenzoyl chloride was added dropwise with stirring andcooling in a water bath. When the reaction was complete, the mixture waswashed with water, dried and the solvent stripped off to give 8.5 g. ofproduct.

EXAMPLE 10 ##STR12##

N,N-bis(2-hydroxyethyl) dichloroacetamide was prepared by reacting 26.3g. of diethanolamine with 37 g. of dichloroacetyl chloride in thepresence of 25.5 g. of triethylamine in 100 ml. of acetone. Then, 6.5 g.of the N,N-bis(2-hydroxyethyl) dichloroacetamide was dissolved in 50 ml.of acetone, then reacted with 4 g. of methyl isocyanate in the presenceof dibutyl tin dilaurate and triethylamine catalysts. The reactionproduct was stripped under vacuum to yield 8.4 g. of product.

EXAMPLE 11 ##STR13##

7.8 g. of diallyl amine was dissolved in 50 ml. of methylene chloride,with 8.5 g. of triethylamine added dropwise. Then, 5.6 g. of malonylchloride was added dropwise with cooling and stirring. When the reactionwas complete, the mixture was washed with water, dried over magnesiumsulfate and stripped under vacuum to yield 7.0 g. of product.

EXAMPLE 12 ##STR14##

7.9 g. of diallyl amine was dissolved in 50 ml. of methylene chloridewith 8.5 g. of triethylamine added dropwise. Then, 6.2 g. of succinylchloride was added dropwise with cooling and stirring. When the reactionwas complete, the mixture was washed with water, dried over magnesiumsulfate and stripped under vacuum to yield 9.7 g. of product.

EXAMPLE 13 ##STR15##

6.7 g. of N-methyl-1-methyl-3-propynylamine was dissolved in 50 ml. ofmethylene chloride with 8.5 g. of triethylamine added dropwise. Then,6.2 g. of succinyl chloride was added dropwise with cooling andstirring. When the reaction was complete, the mixture was washed withwater, dried over magnesium sulfate and stripped under vacuum to yield7.0 g. of product.

EXAMPLE 14 ##STR16##

7.9 g. of diallyl amine was dissolved in 50 ml. of methylene chloridewith 8.5 g. of triethylamine added dropwise. Then, 8.1 g. of o-phthaloylchloride was added dropwise with cooling and stirring. When the reactionwas complete, the mixture was washed with water, dried over magnesiumsulfate and stripped under vacuum to yield 10.9 g. of product.

EXAMPLE 15 ##STR17##

3.3 g. of N-methyl-1-methyl-3-propynylamine was dissolved in 50 ml. ofmethylene chloride with 4.5 g. of triethylamine added dropwise. Then,9.2 g. of diphenyl acetyl chloride was added dropwise with cooling andstirring. When the reaction was complete, the mixture was washed withwater, dried over magnesium sulfate and stripped under vacuum to yield9.9 g. of the product.

EXAMPLE 16 ##STR18##

4.9 g. of diallyl amine was dissolved in 50 ml. of acetone with 7.4 g.of phthalic anhydride added portionwise with stirring. The solvent wasstripped off under vacuum to yield 13.0 g. of product.

EXAMPLE 17 ##STR19##

9.2 g. of N(1,1-dimethyl-3-propynyl)O-phthalamic acid was dissolved in50 ml. of methanol and 9.6 g. of sodium methoxide. 25% in methanol wasadded portionwise with stirring and cooling. The solvent was stripped orremoved under vacuum to yield 9.0 g. of product. The intermediate,N(1,1-dimethyl-3-propynyl)O-phthalamate was prepared from 29.6 g. ofphthalic anhydride and 16.6 g. of 3-amino-3-methylbutyne in 150 ml. ofacetone. The intermediate was precipitated with petroleum ether as awhite solid and used without further purification.

EXAMPLE 18 ##STR20##

A 500 cc. 4-necked flask was provided with stirrer, thermometer andaddition funnel. Then, 7.7 g. of diethylamine (0.105 mole), 4.0 g. ofsodium hydroxide solution and 100 ml. of methylene chloride were chargedto the flask and the mixture was cooled in a dry-ice-acetone bath. Then,14.7 g. (0.10 mole) of dichloroacetyl chloride was added portionwise.The mixture was stirred for an additional hour and immersed in an icebath. It was then phase separated and the lower organic phase was washedwith two portions of 100 ml. of dilute hydrochloric acid, two 100 ml. ofsodium carbonate solutions, dried over magnesium sulfate andconcentrated under vacuum to yield 16.8 g. of product.

EXAMPLE 19 ##STR21##

4.0 g. (0.025 mole) of N,N-diallylcarbamoyl chloride was added to 50 ml.of methylene dichloride. Then, 1.8 g. (0.025 mole) of 2-butyn-1-ol wasadded dropwise with 2.6 g. of triethylamine in 10 ml. methylenechloride. The reaction product was stirred at room temperatureovernight, washed with water twice and dried over magnesium sulfate toyield 4.0 g. of product.

EXAMPLE 20 ##STR22##

9.7 g. (0.1 mole) of potassium thiocyanate was dissolved in 100 ml. ofacetone. Then, 8.7 g. (0.05 mole) of N,N-diallyl chloroacetamide wereadded at room temperature with 10 ml. of dimethyl formamide. Thereaction product was stirred overnight. The reaction product waspartially stripped. Water was added along with two portions of 100 ml.of ether. The ether was separated, dried and stripped to yield 7.2 g. ofproduct.

EXAMPLE 21 ##STR23##

A solution of 50 ml. of benzene containing 7.4 g. (0.05 mole) ofdichloro acetylchloride was formed. To this solution was added 3.0 g.(0.05 mole) of cyclopropylamine and 5.2 g. of triethylamine in 2 ml. ofbenzene at a temperature of 5°-10° C. A precipitate was formed and themixture was stirred for two hours at room temperature and one hour at50°-55° C. The product was worked-up as in previous examples to yield5.7 g. of the product.

EXAMPLE 22 ##STR24##

To 4.7 g. (0.032 mole) of piperonylamine and 1.2 g. of sodium hydroxidein 30 ml. of methylene chloride and 12 ml. of water was added 4.4 g.(0.03 mole) of dichloroacetyl chloride in 15 ml. of methylene chlorideat -5° to 0° C. The mixture was stirred ten more minutes around 0° C.,then allowed to warm to room temperature with stirring. The layers wereseparated and the organic layer washed with dilute hydrochloric acid,10% sodium carbonate solution, water and dried to yield 5.9 g. ofproduct.

EXAMPLE 23 ##STR25##

In a solution of 75 ml. of benzene containing 5.7 g. ofmeta-chlorocinnamyl chloride was formed. To this solution was added 3.2g. of diallyl amine and 3.3 g. of triethyl amine in 2 ml. of benzene ata temperature of 5° to 10° C. A precipitate was formed and the mixturewas stirred for two hours at room temperature and one hour at 55° C. Theproduct was washed and worked up to yield 5.8 g. of product.

EXAMPLE 24 ##STR26##

A 500 cc. 4-necked flask was provided with a stirrer, thermometer andaddition funnel. Then, 11.9 g. 2,4-dimethylpiperidine, 4.0 g. of sodiumhydroxide solution and 100 ml. of methylene chloride were charged to theflask and the mixture cooled in a dry-ice-acetone bath. Then, 14.7 g.(0.10 mole) of dichloroacetyl chloride were added in portions. Themixture was stirred for one hour and immersed in the ice bath, and thenseparated with the lower organic phase washed with two portions of 100ml. of dilute hydrochloric acid and two portions of 100 ml. of 5% sodiumcarbonate solution, dried over magnesium sulfate and concentrated in arotary evaporator under a water pump vacuum to yield 19.3 g. of product.

EXAMPLE 25 ##STR27##

A 500 ml. 4-necked flask was provided with a stirrer, thermometer andaddition funnel. Then, 14.6 g. (0.105 mole) ofcis-trans-decahydroquinoline and 4.0 g. of sodium hydroxide solution and100 ml. of methylene chloride were added together. Then, 14.7 g. ofdichloroacetyl chloride was added portionwise. The reaction mixture wasworked up by stirring for about an hour and immersed in an ice bath andthen phase separated with the lower organic phase being washed with twoportions of 100 ml. dilute hydrochloric acid, two portions of 100 ml. of5% sodium carbonate, dried over magnesium sulfate and concentrated toyield 22.3 g. of product.

EXAMPLE 26 ##STR28##

A 500 ml. 4-necked flask was provided with stirrer, thermometer andaddition funnel. Then, 13.6 g. (0.104 mole) of 3,3'-iminobis-propylaminewas added along with 12.0 g. of sodium hydroxide solution and 150 ml. ofmethylene chloride. Thereafter, the mixture was cooled in a dryice-acetone bath and 44.4 g. (0.300 mole) of dichloroacetyl chloride wasadded portionwise. An oily product formed which :was not soluble inmethylene chloride and was separated and washed with two portions of 100ml. of dilute hydrochloric acid and allowed to stand overnight. The nextmorning the product was washed with two portions of 100 ml. of 5% sodiumcarbonate and the product was taken up in 100 ml. of ethanol, dried overmagnesium sulfate and concentrated to yield 21.0 g. of product.

EXAMPLE 27 ##STR29##

A 500 ml. 4-necked flask was provided with stirrer, thermometer andaddition funnel. Then, 7.5 g. of tetrahydrofurfuryl-n-propylamine(0.0525 mole) and 2.0 g. sodium hydroxide solution and 100 ml. ofmethylene chloride were charged thereto. Then, 7.4 g. (0.05 mole) ofdichloroacetyl chloride were added portionwise. The mixture was stirredfor one additional hour in an ice bath and then separated with the lowerorganic phase washed with two portions of 100 ml. of dilute hydrochloricacid and two portions of 100 ml. of 5% sodium carbonate solution, driedover magnesium sulfate and concentrated to yield 12.7 g. of product.

EXAMPLE 28 ##STR30##

Example 27 was repeated in its entirety except that 8.9 g. of piperidinewas used as the amine.

EXAMPLE 29 ##STR31##

Example 28 was essentially repeated in its entirety except 9.1 g. ofmorpholine was used as the amine.

EXAMPLE 30 ##STR32##

3.2 g. of benzaldehyde and 7.7 g. of dichloracetamide were combined with100 ml. of benzene and approximately 0.05 g. of paratoluene sulfonicacid. The mixture was refluxed until water ceased to come over. Oncooling the product crystallized from benzene yielding 7.0 g. ofproduct.

EXAMPLE 31 ##STR33##

2.5 g. of 3-amino-3-methylbutyne was dissolved in 50 ml. of acetone and3.5 g. of triethylamine was added, followed by 6.0 g. ofadamantane-1-carbonyl chloride added dropwise with stirring and cooling.The mixture was poured into water and the solid product collected byfiltration and dried under vacuum to give 6.5 g. of product.

EXAMPLE 32 ##STR34##

5.1 g. of 2-cyanoisopropylamine was dissolved in 50 ml. of acetone with6.5 g. of triethylamine added, followed by 5.3 g. ofbenzene-1,3,5-tricarboxylic acid chloride added dropwise with stirringand cooling. The mixture was poured into water and the solid productcollected by filtration and dried under vacuum to give 7.6 g. ofproduct.

EXAMPLE 33 ##STR35##

6.0 g. of diallylamine was dissolved in 50 ml. of methylene chloride,6.5 g. of triethylamine was added and 6.6 g. of3,6-endomethylene-1,2,3,6-tetrahydrophthaloyl chloride was addeddropwise with stirring and cooling. When the reaction was complete themixture was washed with water, dried over magnesium sulfate and strippedunder vacuum to yield 9.3 g. of product.

EXAMPLE 34 ##STR36##

4.0 g. of diallylamine was dissolved in 50 ml. of methylene chloride,4.5 g. of triethylamine was added and 7.2 g. oftrans-2-phenylcyclopropane carbonyl chloride was added dropwise withcooling and stirring. When the reaction was complete the mixture waswashed with water, dried over magnesium sulfate and stripped undervacuum to yield 9.3 g. of product.

EXAMPLE 35 ##STR37##

A solution was formed consisting of 4.0 g. (0.03 mole) of 2-methylindoline, 7.0 ml. triethylamine and 100 ml. of methylene chloride. Then,2.9 ml. of dichloroacetyl chloride was added thereto over a period ofabout one minute with dry ice cooling, keeping the temperature under 0°C. The solution was allowed to warm to room temperature and stand forone hour and then washed with water and then with dilute hydrochloricacid, dried over magnesium sulfate and evaporated to give a solid thatwas washed with n-pentane to give 5.0 g. of product.

EXAMPLE 36 ##STR38##

A 500 cc. 4-necked flask was provided with stirrer, thermometer andaddition funnel. Then, 8.9 g. of cyclooctyl n-propylamine, 2.0 g. ofsodium hydroxide solution and 100 ml. of methylene chloride were chargedto the flask and the mixture was cooled in a dry ice-acetone bath. Then,5.6 g. of chloroacetyl chloride was added portionwise. The mixture wasstirred for about one additional hour, immersed in the ice bath, thenphase separated and the lower organic phase was washed with two portionsof 100 ml. of dilute hydrochloric acid and two portions of 100 ml. 5%sodium carbonate solution, dried over magnesium sulfate and concentratedto yield 9.5 g. of product.

EXAMPLE 37 ##STR39##

A 500 cc. 4-necked flask was provided with stirrer, thermometer andaddition funnel. Then, 7.8 g. (0.0525 mole) of p-methylbenzylethylamine, 2.0 g. of sodium hydroxide solution and 100 ml. of methylenechloride were charged to the flask. The mixture was cooled in a dryice-acetone bath. Then, 5.6 g. (0.05 mole) of chloroacetyl chloride wasadded portionwise. The mixture was stirred for about one additionalhour, immersed in the ice bath, then phase separated with the lowerorganic phase being washed with two portions of 100 ml. of dilutehydrochloric acid and then two portions of 100 ml. of 5% sodiumcarbonate solution, dried over magnesium sulfate and concentrated toyield 9.5 g. of product.

EXAMPLE 38 ##STR40##

4.7 g. of amino pyridine were charged to a reaction vessel along with100 ml. of acetone and stirred at 10°-15° C. Then, 7.0 ml. oftriethylamine were added dropwise. Thereafter, 5.25 ml. ofdichloroacetyl chloride in 10 ml. of acetone was added over a period offive minutes and stirred at room temperature. The solids were filteredoff, washed with acetone to yield 10.0 g. of product.

EXAMPLE 39 ##STR41##

8.1 g. (0.05 mole) of 4-aminophthalimide was dissolved in 100 ml. ofdimethylfuran, wherein 5.0 g. of dichloroacetyl chloride was stirred inat 0°-10° C. over a period of 5 minutes. Then, 7.0 ml. of triethylaminewas added. The reaction mass was stirred for one-half hour at roomtemperature and then one liter of water was added. The reaction wasfiltered with water and dried to give 12.0 g. of product.

EXAMPLE 40 ##STR42##

The compound of this example was prepared by reacting 5.4 g. ofN,N-bis(2-hydroxyethyl) dichloroacetamide with 4.3 g. of isopropylisocyanate in 50 ml. of acetone in the presence of dibutyltin dilaurateand triethylenediamine catalysts, to yield 8.2 g. of product.

EXAMPLE 41 ##STR43##

The compound of this example was prepared by reacting 3.6 g. ofN,N-bis(2-hydroxyethyl) chloroacetamide with 5.0 g. of cyclohexylisocyanate in the presence of 50 ml. of acetone and dibutyltin dilaurateand triethylenediamine catalysts. The reaction mass was heated to refluxand stripped under vacuum to yield 6.9 g. of product.

EXAMPLE 42 ##STR44##

15 g. of acetone and 12.2 g. of ethanol amine were combined in 150 ml.of benzene and refluxed until no additional water came over. Theresulting solution was examined and found to contain2,2-dimethyl-1,3-oxazolidine. A quarter of the benzene solution (0.05mole) was reacted with 7.4 g. of dichloroacetyl chloride and 5.5 g. oftriethylamine, washed with water, dried and stripped under vacuum togive a light tan solid. A portion was recrystallized from ether giving awhite product.

Other compounds were prepared in an analogous manner starting with theappropriate starting materials as outlined above. The following is atable of compounds representative of those embodied by the presentinvention. Compound numbers have been assigned to them and are used foridentification throughout the balance of the specification.

    TABLE I      ##STR45##      Compound No. R R.sub.1 R.sub.2      1 CH(CH.sub.3)Br CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2 2 C(CH.sub.3).sub     .2 Br " " 3 CCl.sub.2CH.sub.3 " " 4 CClCCl.sub.2 " " 5 CF.sub.2C.sub.2     F.sub.5 " " 6 CHCl.sub.2 " " 7 CH.sub.2 Cl " " 8 CHCl.sub.2 CH.sub.2CN     CH.sub.CN 9 CHCl.sub.2 CH.sub.2CHCH.sub.2 H 10 CHCl.sub.2 C.sub.3     H.sub.7 C.sub.3 H.sub.7 11 CHCl.sub.2 C(CH.sub.3).sub.2CN H 12 CH.sub.2     Cl " " 13 CCl.sub.3 CH.sub.2CHCH.sub.2 " 14 CCl.sub.3 " CH.sub.2CHCH.sub.     2 15 CH.sub.2      Cl C(CH.sub.3).sub.2CCH H 16 CHCl.sub.2 C(CH.sub.3).sub.2CCH H 17     CCl.sub.3 " " 18 CHCl.sub.2 CH.sub.3 CH(CH.sub.3)CCH  19 CHCl.sub.2     CH.sub.2CHCH.sub.2      ##STR46##       20 CH.sub.2      Cl H     ##STR47##       21 CHCl.sub.2 " "  22 CH.sub.2      Cl "     ##STR48##       23 CHCl.sub.2 " "      24 CHCl.sub.2 "     ##STR49##      25  CHCl.sub.2 "     ##STR50##      26 CHCl.sub.2 "     ##STR51##      27 CHCl.sub.2 H     ##STR52##      28 CHCl.sub.2 "     ##STR53##      29     ##STR54##      CH.sub.3 CH(CH.sub.3)CCH  30 " CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2 31 C     H.sub.2CH(CH.sub.3)CH.sub.2 -t-C.sub.4 H.sub.9 H C(CH.sub.3).sub.2CCH 32 C     (CH.sub.3).sub.2C.sub.3 H.sub.7 CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2 33 C     H.sub.2 -t-C.sub.4 H.sub.9 CH.sub.3 CH(CH.sub.3)CCH 34 CH.sub.2      -t-C.sub.4 H.sub.9 H C(CH.sub.3).sub.2CN 35 CH(CH.sub.3)C.sub.3 H.sub.7 C     H.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2 36 " CH.sub.3 CH(CH.sub.3)CCH 37 "     H C(CH.sub.3).sub.2CCH 38 i-C.sub.3 H.sub.7 CH.sub.3 CH(CH.sub.3)CCH 39     C.sub.13 H.sub.27 CH.sub.2CHCH.sub.2 CH.sub.2 CHCH.sub.2 40 C.sub.11     H.sub.23 " " 41 " H C(CH.sub.3).sub.2CCH 42 C.sub.9      H.sub.19 CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2 43 " H C(CH.sub.3).sub.2CC     H 44 C.sub.6 H.sub.13 CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.3 45 "     CH.sub.3 CH(CH.sub.3)CCH 46 " H C(CH.sub.3).sub.2CCH 47 C.sub.4 H.sub.9     H " 48 C.sub.3 H.sub.7 CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2 49 "     CH.sub.3 CH(CH.sub.3)CCH 50 " H (CH.sub.3).sub.2 CCH 51 CH.sub.3         C     CH.sub.2HCH.sub.2 CH.sub.2CHCH.sub.2 52 CH.sub.3 H C(CH.sub.3).sub.2CCH     53 C(CH.sub.3)CH.sub.2 H " 54 CHCHCH.sub.3 CH.sub.2CHCH.sub.2 CH.sub.2CHC     H.sub.2 55 " H C(CH.sub.3).sub.2CCH 56 CHC(CH.sub.3).sub.2 CH.sub.3     CH(CH.sub.3)CCH 57 " H C(CH.sub.3).sub.2CCH 58 CHCHCHCHCH.sub.3 CH.sub.2C     HCH.sub.2 CH.sub.2CHCH.sub.2 59 " H C(CH.sub.3).sub.2 CCH      60     ##STR55##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  61 " CH.sub.3 CH(CH.sub.3)CCH     62 " H C(CH.sub.3).sub.2CCH      63     ##STR56##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  64 " CH.sub.3 CH(CH.sub.3)CCH     65      ##STR57##      H C(CH.sub.3).sub.2CCH      66     ##STR58##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  67 " CH.sub.3 CH(CH.sub.3)CCH     68      ##STR59##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  69 " CH.sub.3 CH(CH.sub.3)CCH 70     " H C(CH.sub.3).sub.2CCH      71     ##STR60##      CH.sub.2CHCH.sub.2 CH.sub.2 CHCH.sub.2      72 CHCH.sub.2 CH.sub.3 CH(CH.sub.3)CCH 73 " H C(CH.sub.3).sub.2CCH  74      ##STR61##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      75     ##STR62##      CH.sub.3 CH(CH.sub.3)CCH  76 " H C(CH.sub.3).sub.2CH      77     ##STR63##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  78 " CH.sub.3 CH(CH.sub.3)CCH     79      ##STR64##      CH.sub.3 " 80 " H C(CH.sub.3).sub.2C CH 81 CBr.sub.3 CH.sub.2CHCH.sub.2 C     H.sub.2CHCH.sub.2 82 " CH.sub.3 CH(CH.sub.3)CH 83 " H C(CH.sub.3).sub.2CC     H 84 " " C(CH.sub.3).sub.2CN 85 " H CH.sub.2CHCH.sub.2 86 CClCHCl     CH.sub.3 CH(CH.sub.3)CCH 87 (CH.sub.2).sub.4CH.sub.2Br CH.sub.2      CHCH.sub.2 CH.sub.2 CHCH.sub.2 88 " CH.sub.3 CH(CH.sub.3)CCH  89      ##STR65##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  90 " CH.sub.3 CH(CH.sub.3)C CH     91      ##STR66##      " "      92     ##STR67##      CH.sub.2 CHCH.sub.2 CH.sub.2 CHCH.sub.2  93 " CH.sub.3 CH(CH.sub.3)CCH     94 " H C(CH.sub.3).sub.2CCH      95     ##STR68##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  96 " H C(CH.sub.3).sub.2CCH  97      ##STR69##      CH.sub.3 CH(CH.sub.3)CCH  98 " H C(CH.sub.3).sub.2CCH      99     ##STR70##      CH.sub.3 CH(CH.sub.3)CCH  100 " H C(CH.sub.3).sub.2CCH      101     ##STR71##      CH.sub.3 CH(CH.sub.3)CCH  102 " H C(CH.sub.3).sub.2CCH      103     ##STR72##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      104     ##STR73##      CH.sub.3 CH(CH.sub.3)CCH      105     ##STR74##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  106 " CH.sub.3 CH(CH.sub.3)CCH     107 " H C(CH.sub. 3).sub.2CCH      108     ##STR75##      CH.sub.3 CH(CH.sub.3)CCH  109 " H C(CH.sub.3).sub.2CCH      110     ##STR76##      CH.sub.3 CH(CH.sub.3)CCH      111     ##STR77##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      112     ##STR78##      CH.sub.3 CH(CH.sub.3)CCH      113     ##STR79##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  114 " H C(CH.sub.3).sub.2CCH     115      ##STR80##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  116 " H C(CH.sub.3).sub.2CCH 117 C     HCl.sub.2 C.sub.2 H.sub.4 OH C.sub.2 H.sub.4 OH      118 "     ##STR81##      ##STR82##       119 " CH.sub.2CH.sub.2OSO.sub.2CH.sub.3 CH.sub.2CHOSO.sub.2CH.sub.3     120      ##STR83##      CH.sub.3 CH(CH.sub.3)CCH      121     ##STR84##      " "                                                                     C    C      122 CHBrCH.sub.3 CH.sub.3 CH(CH.sub.3)CCH 123 " H C(CH.sub.3).sub.2H     124 CH.sub.2CH.sub.2 Cl CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2 125 "     CH.sub.3 CH(CH.sub.3)CCH 126 " H C(CH.sub.3).sub.2CCH 127 CBr(CH.sub.3).s     ub.2 H " 128 CH.sub.2 I CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2 129 "     CH.sub.3 CH(CH.sub.3)CCH 130 " H C(CH.sub.3).sub.2CCH 131 CHCl.sub.2     CH.sub.2CH.sub.2 Cl CH.sub.2CH.sub.2 Cl      132 "     ##STR85##      ##STR86##      133 "     ##STR87##      ##STR88##      134 CHCl.sub.2     ##STR89##      ##STR90##      135 "     ##STR91##      ##STR92##      136     ##STR93##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  137 " CH.sub.3 CH(CH.sub.3)CCH     138 " H C(CH.sub.3).sub.2CCH      139     ##STR94##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  140 " CH.sub.3 CH(CH.sub.3)CCH     141      ##STR95##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  142 " CH.sub.3 CH(CH.sub.3)CCH     143      ##STR96##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      144     ##STR97##      CH.sub.3 CH(CH.sub.3)CCH      145     ##STR98##      H C(CH.sub.3).sub.2CCH      146     ##STR99##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      147     ##STR100##      CH.sub.3 CH(CH.sub.3)CCH      148     ##STR101##      H C(CH.sub.3).sub.2CCH      149     ##STR102##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      150     ##STR103##      CH.sub.3 CH(CH.sub.3)CCH      151     ##STR104##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      152     ##STR105##      CH.sub.3 CH(CH.sub.3)CCH      153     ##STR106##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      154     ##STR107##      CH.sub.3 CH(CH.sub.3)CCH      155     ##STR108##      CH.sub.3 "      156     ##STR109##      H C(CH.sub.3).sub.2CCH      157     ##STR110##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      158     ##STR111##      CH.sub.3 CH(CH.sub.3CCH      159     ##STR112##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      160     ##STR113##      CH.sub.3 CH(CH.sub.3)CCH      161     ##STR114##      H C(CH.sub.3).sub.2C CH      162     ##STR115##      CH.sub.3 CH(CH.sub.3)CCH      163     ##STR116##      CH.sub.2 CHCH.sub.2 CH.sub.2 CHCH.sub.2      164     ##STR117##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      165     ##STR118##      H C(CH.sub.3).sub.2CCH      166     ##STR119##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      167     ##STR120##      H C(CH.sub.3).sub.2CCH      168     ##STR121##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  169 " CH.sub.3 CH(CH.sub.3)CCH     170 " H C(CH.sub.3).sub.2CCH      171     ##STR122##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  172 " CH.sub.3 CH(CH.sub.3)CCH     173 " H C(CH.sub.3).sub.2CH      174     ##STR123##      CH.sub.3 CH(CH.sub.3)CCH      175     ##STR124##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  176 " H C(CH.sub.3).sub.2 CCH     177      ##STR125##      H "      178     ##STR126##      H "  179 CHCl.sub.2 C.sub.2 H.sub.5 C.sub.2 H.sub.5 180 " i-C.sub.3     H.sub.7 CH.sub.2CHCH.sub.2 181 " C.sub.3 H.sub.7 " 182 " n-C.sub.4     H.sub.9 " 183 CHCl.sub.2 CH.sub.2CHCH.sub.2 CH.sub.2CClCH.sub.2 184 "     C.sub.3 H.sub.7 " 185 " i-C.sub.4 H.sub.9 CH.sub.2CHCH.sub.2 186 "     CH.sub.2C(CH.sub.3)CH.sub.2 " 187 CHCl.sub.2 n-C.sub.4      H.sub.9 sec-C.sub.4 H.sub.9 188 " " i-C.sub.4 H.sub.9 189 " " i-C.sub.3     H.sub.7 190 " i-C.sub.4 H.sub.9 " 191 " " n-C.sub.3 H.sub.7 192 "     sec-C.sub.4 H.sub.9  " 193 " n-C.sub.4 H.sub.9 " 194 " C.sub.2 H.sub.5       i-C.sub.4 H.sub.9      195 CHCl.sub.2 H     ##STR127##       196 " CH.sub.3 NH.sub.2  197 Cl CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2     198 CHCl.sub.2 C[N(CH.sub.3).sub.2 ].sub.2 199 CH.sub.2 Cl " 200     OCH.sub.2CCCH.sub.3 CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2 201 OC.sub.2     H.sub.4 Cl " " 202 OCH.sub.2CHCl.sub.2 " "      203     ##STR128##      " "  204 CH.sub.2SCN " " 205 CH.sub.2N(CH.sub.2CHCH.sub.2).sub.2 " "     206 CHCl.sub.2 H      ##STR129##      207 CHCl.sub.2 CH.sub.3     ##STR130##      208     ##STR131##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2                                   N      209 CH.sub.2CN " " 210 CH.sub.2OC " "  211 CHCl.sub.2 C.sub.2 H.sub.5      ##STR132##       212 " CH.sub.2CH.sub.2C N CH.sub.2CHCN      213 " H     ##STR133##      214 " "     ##STR134##      215 CHCl.sub.2 H     ##STR135##      216 " "     ##STR136##       217 CH.sub.2 Cl " CH.sub.2CH(CH.sub.3).sub.2  218 CHCl.sub.2 "      ##STR137##       219 CHCl.sub.2 H i-C.sub.4 H.sub.9 220 CH.sub.2 Cl " t-C.sub.4 H.sub.9     221 CHCl.sub.2 " " 222 CH.sub.2      Cl " CH(CH.sub.3)CH.sub.2CH(CH.sub.3)CH.sub.3  223 CHCl.sub.2 "      ##STR138##      224 CHCl.sub.2 H     ##STR139##      225 " "     ##STR140##      226 " "     ##STR141##      227 " "     ##STR142##      228     ##STR143##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      229     ##STR144##      " "      230     ##STR145##      " "      231     ##STR146##      " "      232 CHCl.sub.2     ##STR147##      CH.sub.2CHCH.sub.2 233 "     t-C.sub.4 H.sub.9 CHCHCH.sub.2CH.sub.3 234 " C(C.sub.3).sub.2C CH "  235     " C.sub.2      H.sub.5     ##STR148##       236 " n-C.sub.4 H.sub.9 CHCHCH.sub.2CH.sub.3      237 "     ##STR149##      n-C.sub.3 H.sub.7      238 " C(CH.sub.3)CHCH.sub.2CH.sub.3 " 239 CH.sub.2SO.sub.2N(CH.sub.2CHCH     .sub.2) CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2 240 CH(SC.sub.2      H.sub.5).sub.2 " " 241 CHCl.sub.2 CH.sub.3 NC(CH.sub.3).sub.2  242      ##STR150##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      243     ##STR151##      " "  244 CHCl.sub.2 sec-C.sub.4 H.sub.9 C.sub.2 H.sub.5 245 " t-C.sub.4     H.sub.9 " 246 " sec-C.sub.4 H.sub.11 " 247 " i-C.sub.3 H.sub. 7 "  248 " C     H.sub.3      ##STR152##       249 " C.sub.2 H.sub.5 "  250 " n-C.sub.3      H.sub.7     ##STR153##       251 " CH.sub.3 sec-C.sub.5 H.sub.11 252 " n-C.sub.3 H.sub.7 " 253     CHCl.sub.2     n-C.sub.3 H.sub.7 n-C.sub.5 H.sub.11 254 " i-C.sub.4 H.sub.9 sec-C.sub.4     H.sub.9 255 " CH.sub.3 i-C.sub.3                                         C      H.sub.7 256 " " CH(CH.sub.3)CH(CH.sub.3)H.sub.3  257 " C.sub.2 H.sub.5      ##STR154##      258 ""     ##STR155##      259 " "     ##STR156##       260 " CH.sub.3 sec-C.sub.4 H.sub.9 261 " C.sub.2 H.sub.5 n-C.sub.6     H.sub.13 262 "  n-C.sub.3 H.sub.7 t-C.sub.4      H.sub.9 263 " " CH(CH.sub.3)CH(CH.sub.3)CH.sub.3  264 CHCl.sub.2     n-C.sub.3      H.sub.7     ##STR157##      265 " "     ##STR158##      266 " "     ##STR159##      267 " "     ##STR160##       268 " C.sub.2      H.sub.5     ##STR161##

    TABLE I      ##STR162##      Compound No. R R.sub.1 R.sub.2         269 "      ##STR163##      270 "     ##STR164##      271 CHCl.sub.2     ##STR165##      272 "     ##STR166##      273 "     ##STR167##      274 "     ##STR168##      275 "     ##STR169##      276 "     ##STR170##      277 CHCl.sub.2     ##STR171##      278 "     ##STR172##       279 "     ##STR173##      280 "     ##STR174##          281 " CH.sub.3     ##STR175##      282 " "     ##STR176##      283 " "     ##STR177##       284 CHCl.sub.2 C.sub.2      H.sub.5     ##STR178##       285 " n-C.sub.3      H.sub.7     ##STR179##         286 "     ##STR180##      287 "     ##STR181##          288 " H     ##STR182##       289 " C.sub.2 H.sub.5 "      290 "     ##STR183##      ##STR184##      291 CHCl.sub.2     ##STR185##      ##STR186##      292 " CH.sub.2CHCH.sub.2     ##STR187##       293 " C.sub.2 H.sub.5 "  294 " n-C.sub.3      H.sub.5     ##STR188##      295 "     ##STR189##      n-C.sub.3 H.sub.7      296 "     ##STR190##      n-C.sub.3 H.sub.7  297 " n-C.sub.3      H.sub.7     ##STR191##       298 " " n-C.sub.6 H.sub.13  299 " C.sub.2 H.sub.4OCH.sub.3 C.sub.2     H.sub.4OCH.sub.3 300 CHCl.sub.2 C.sub.2 H.sub.4OC.sub.2 H.sub.5 C.sub.2     H.sub.4OC.sub.2 H.sub.5  301 " C.sub.2      H.sub.5     ##STR192##       302 " n-C.sub.3 H.sub.7 " 303 " i-C.sub.3 H.sub.7 " 304 " n-C.sub.4     H.sub.9 "         305 "     ##STR193##      306 "     ##STR194##      307 "     ##STR195##      308 "     ##STR196##          309 CHCl.sub.2 CH.sub.3     ##STR197##       310 " C.sub.2 H.sub.5 " 311 " n-C.sub.3 H.sub.7 " 312 " i-C.sub.3     H.sub.7 " 313 " n-C.sub.4 H.sub.9 " 314 " sec-C.sub.4 H.sub.9 " 315 "     t-C.sub.4 H.sub.9 CH.sub.2CH.sub.2 OH 316 " CH.sub.3 CH.sub.2CH.sub.2CN        317 "      ##STR198##       318 " n-C.sub.6 H.sub.13 n-C.sub.6      H.sub.13 319 " CH.sub.3 CH.sub.2CH.sub.2 OH         320 "     ##STR199##          321 CHCl.sub.2 CH.sub.2CH.sub.2SH     ##STR200##       322 " H C(C.sub.2 H.sub.5).sub.2CN  323 CH.sub.2 Cl " "      324  CHCl.sub.2 "      ##STR201##      325 " "     ##STR202##      326 " "     ##STR203##       327 CH.sub.2 Cl " "      328 CHCl.sub.2 "     ##STR204##      329 CHCl.sub.2 H     ##STR205##      330 " "     ##STR206##      331 " "     ##STR207##       332 " " CH.sub.2C(CH.sub.3)CH.sub.2 333 CH.sub.2 Cl " " 334 CHCl.sub.2     " CH.sub.2CH.sub.2OCH.sub.3      335 " "     ##STR208##       336 CH.sub.2      Cl CH.sub.3 CH.sub.2CCH 337 CHCl.sub.2 CH.sub.3 CH.sub.2CCH  338 " H      ##STR209##       339 " " CH.sub.2CH.sub.2N(C.sub.2      H.sub.5).sub.2 340 " " CH.sub.2CH(OCH.sub.3).sub.2      341 " "     ##STR210##      342     ##STR211##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      343 CHCl.sub.2 H     ##STR212##      344 " "     ##STR213##      345 " "     ##STR214##      346 CHCl.sub. 2 H     ##STR215##      347 " "     ##STR216##      348 " "     ##STR217##      349     ##STR218##      " C(CH.sub.3).sub.2CN      350     ##STR219##      " C(CH.sub.3).sub.2CCH  351 " " C(CH.sub.3).sub.2 CN      352     ##STR220##      CH.sub.2CHCH.sub.2 CH.sub. 2CHCH.sub.2      353     ##STR221##      H C(CH.sub.3).sub.2CN      354     ##STR222##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      355     ##STR223##      H C(CH.sub.3).sub.2CCH  356 " " C(CH.sub.3).sub.2CN      357     ##STR224##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      358     ##STR225##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      359     ##STR226##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      360     ##STR227##      H C(CH.sub.3).sub.2CCH      361     ##STR228##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2  362 " H C(CH.sub.3).sub.2CCH     363      ##STR229##      H C(CH.sub.3).sub.2C CH  364 CHCl.sub.2 H C(CH.sub.3)CHCN      365     ##STR230##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2      366 CHCl.sub.2 H     ##STR231##         367 "     ##STR232##          368 CHCl.sub.2     ##STR233##      CH.sub.2CH(CH.sub.3).sub.2  369 " CHO "      370     ##STR234##      H C(CH.sub.3).sub.3      371     ##STR235##      " "      372     ##STR236##      " C(CH.sub.3).sub.2C CH      373     ##STR237##      CH.sub.3 CH(CH.sub.3)CCH      374     ##STR238##      H C(CH.sub.3).sub.2CN      375     ##STR239##      " "  376 CH.sub.2C(CH.sub.3).sub.3 H C(CH.sub.3).sub.2CN      377     ##STR240##      " C(CH.sub.3).sub.2CCH      378     ##STR241##      " "      379     ##STR242##      H C(CH.sub.3).sub.2CCH      380     ##STR243##      " C(CH.sub.3).sub.2CN  381 " CH.sub.3 CH(CH.sub.3)CCH      382     ##STR244##      H C(CH.sub.3).sub.2CCH      383     ##STR245##      " C(CH.sub.3).sub.2CN       384 H H     ##STR246##      385     ##STR247##      CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.2         386 CHCl.sub.2     ##STR248##           387 CH.sub.2      Cl H     ##STR249##      388 CCl.sub.3 "     ##STR250##      389 CHCl.sub.2 "     ##STR251##      390 ""     ##STR252##      391 CHCl.sub.2 H     ##STR253##      392 " "     ##STR254##      393 " "     ##STR255##       394 CH.sub.3 " C(CF.sub.3).sub.2OH      395 CHCl.sub.2 "     ##STR256##      396 ""     ##STR257##      397 CH.sub.2 OC(CHCl.sub.2).sub.2OH CH.sub.2CHCH.sub.2 CH.sub.2CHCH.sub.     2 398 CH.sub.2OC(CHCl.sub.2)(CCl.sub.3)OH " "  399 CH.sub.2 Cl H      ##STR258##      400     ##STR259##      "      ##STR260##      401     ##STR261##      "      ##STR262##       402 CH.sub.2 Cl n-C.sub.4 H.sub.9 CHCH.sub.2      403     ##STR263##      H      ##STR264##       404 CH.sub.2 Cl CH.sub.3 CH.sub.2CH.sub.2C N 405 " n-C.sub.6 H.sub.13     n-C.sub.6 H.sub.13  406 " C.sub.2      H.sub.5     ##STR265##       407 CH.sub.2 Cl n-C.sub.3      H.sub.7     ##STR266##       408 " i-C.sub.3 H.sub.7 "      409 " CH.sub.3     ##STR267##      410 " "     ##STR268##       411 " C.sub.2      H.sub.5     ##STR269##       412 " n-C.sub.3      H.sub.7     ##STR270##         413 "     ##STR271##       414 CH.sub.2      Cl     ##STR272##      415 "     ##STR273##       416 "  CH.sub.3 i-C.sub.3      H.sub.7 417 " " CH(CH.sub.3)CH(CH.sub.3)CH.sub.3  418 " C.sub.2 H.sub.5      ##STR274##       419 " n-C.sub.3 H.sub.7 i-C.sub.4 H.sub.9 420 " " sec-C.sub.5 H.sub.11     421 " " t-C.sub.4 H.sub.9 422 " i-C.sub.4 H.sub.9 sec-C.sub.4 H.sub.9     423 " C.sub.2 H.sub.5 " 424 CH.sub.2 Cl i-C.sub.4 H.sub.9 i-C.sub.3     H.sub.7 425 " n-C.sub.4 H.sub.9 " 426 " " i-C.sub.4 H.sub.9 427 "     CH.sub.2CH.sub.2OCH.sub.3 CH.sub.2CH.sub.2OCH.sub.3 428 " CH.sub.2CH.sub.     2OC.sub.2 H.sub.5 CH.sub.2CH.sub.2OC.sub.2 H.sub.5      429 "     ##STR275##     n-C.sub.3 H.sub.7      430 "     ##STR276##      "      431 "                                                                n-C     .sub.3      H.sub.7     ##STR277##      432 " "     ##STR278##      433 " "     ##STR279##       434 CH.sub.2 Cl C.sub.2      H.sub.5     ##STR280##       435 " C.sub.2      H.sub.5     ##STR281##       436 " n-C.sub.3      H.sub.7     ##STR282##       437 " C.sub.2      H.sub.5     ##STR283##      438 " CH.sub.3     ##STR284##       439 CHCl.sub.2 CH.sub.3 "  440 " C.sub.2      H.sub.5     ##STR285##       441 CHCl.sub.2 n-C.sub.3      H.sub.7     ##STR286##       442 " C.sub.2      H.sub.5     ##STR287##      443 ""     ##STR288##       444 "CH.sub.3 n-C.sub.4 H.sub.9 445 CH.sub.2 Cl " " 446 CHCl.sub.2 "     sec-C.sub.4 H.sub.9 447 CH.sub.2 Cl " " 448 CHCl.sub.2 " n-C.sub.3     H.sub.7 449 CH.sub.2      Cl " " 450 CHCl.sub.2                               n-C.sub.4 H.sub.9     t-C.sub.4 H.sub.9 451 CHCl.sub.2 i-C.sub.3 H.sub.7 sec-C.sub.4 H.sub.9     452 CH.sub.2 Cl " " 453 CHCl.sub.2 " n-C.sub.4 H.sub.11 454 CH.sub.2 Cl     " " 455 CHCl.sub.2 " sec-C.sub.5 H.sub.11      456 CHCl.sub.2 H     ##STR289##      457 " "     ##STR290##      458 " "     ##STR291##      459 " "     ##STR292##      460 CHCl.sub.2 H     ##STR293##      461 " CH.sub.2OCH.sub.3     ##STR294##      462 " H     ##STR295##      463 " "     ##STR296##      464 " CHO     ##STR297##      465 CHCl.sub.2 CH.sub.2CH(CH.sub.3).sub.2     ##STR298##       466 " H  (CH.sub.2).sub.3OCH(CH.sub.3).sub.2  467 CHCl.sub.2 H      ##STR299##       468 " " C(C.sub.2 H.sub.5)(CH.sub.3).sub.2      469 " "     ##STR300##       470 CH.sub.2 Cl " C(C.sub.2 H.sub.5)(CH.sub.3).sub.2 471 " " C.sub.2     H.sub.4OCH.sub.3 472 " " CH.sub.2CH(OCH.sub.3).sub.2      473     ##STR301##      " C(CH.sub.3).sub.2CN      474     ##STR302##      " C(CH.sub.3).sub.2CCH      475 CHCl.sub.2     ##STR303##      ##STR304##      476 CHCl.sub.2     ##STR305##      ##STR306##      477 "     ##STR307##      ##STR308##      478 "     ##STR309##      ##STR310##      479 "     ##STR311##      ##STR312##       480 CH.sub.2      Cl     ##STR313##      ##STR314##      481 "     ##STR315##      ##STR316##      482 "     ##STR317##      ##STR318##      483 "     ##STR319##      ##STR320##       484 CHCl.sub.2 H CH.sub.2CH.sub.2OH 485 CH.sub.2 Cl CH.sub.2CH.sub.2OH     " 486 CHCl.sub.2 H CH.sub.2CH(OH)(CH.sub.3) 487 " " (CH.sub.2).sub.3OH     488 " CH.sub.2CH(OH)(CH.sub.3) CH.sub.2CH(OH)(CH.sub.3)     489 "      ##STR321##       490 CH.sub.2 OH C.sub.2 H.sub.5 C.sub.2 H.sub.5      491 CH.sub.3     ##STR322##      ##STR323##      492     ##STR324##      H CH.sub.2CH(CH.sub.3).sub.2  493 CH.sub.2SO.sub.2OCH.sub.3 C.sub.2     H.sub.5 C.sub.2 H.sub.5 494 C.sub.3 H.sub.6 Br H SO.sub.2 Cl    495     CHCl.sub.2      ##STR325##       496 CCl.sub.3 C.sub.3 H.sub.7 C.sub.3      H.sub.7    497 "     ##STR326##      498 "     ##STR327##       499 CH.sub.2 Cl " 500 CCl.sub. 3 CH.sub.3 CH.sub.3 501 CH.sub.2 Cl H     C.sub.2 H.sub.4 Br 502 CCl.sub.3 " " 503 CHCl.sub.2 " " 504 CHCl.sub.2     C.sub.2      H.sub.5                                                          n-C.sub     .4      H.sub.9 505 "                                                         i-     C.sub.3      H.sub.7                                                          i-C.sub     .3      H.sub.7 506 "                                                         n-     C.sub.4      H.sub.9                                                          n-C.sub     .4 H.sub.9 507 CCl.sub.3 C.sub.2      H.sub.5 " 508 "                         i-C.sub.3      H.sub.7               i-C.sub.3      H.sub.7 509 "                           i-C.sub.4      H.sub.9               i-C.sub.4 H.sub.9      510 CHCl.sub.2 H     ##STR328##       511 CCl.sub.3 " C(CH.sub.3)(C.sub.2 H.sub.5)CN 512 CH.sub.2 Cl " " 513 C     HCl.sub.2 " "

The compositions of this invention were tested in the following manner.

Test 1: Soil Incorporation

Small flats were filled with Felton loamy sand soil. The herbicide andherbicide antidote were applied separately or in combination to the soilas it is mixed in a five-gallon cement mixer. The following stocksolutions were made up of each compound when the herbicide and antidotewere applied separately. Stock solutions of the herbicide were dilutedwith 100 ml. of water. For the antidote, 700 mg. of technical materialwas diluted with 100 ml of acetone. One ml. of these stock solutions isequivalent to 7 mg. active ingredient or one pound per acre when thistreated soil was placed into 8×12×3" flats. After the soil was treatedwith the herbicide and the antidote at the desired rates, the soil wastransferred from the cement mixer back into 8×12×3" flats where it wasnow ready for planting corn seed. A pint sample of soil was then removedfrom each flat and retained for covering the seeds after planting. Thesoil was leveled and rows one-half inch deep were made in each flat.Enough seeds were planted to obtain good stands in each treatment. Seedswere then covered up with the one pint of soil which had been removedjust prior to planting.

The flats were then placed on greenhouse benches where temperatures werebetween 70°-90° F. The flats were watered by sprinkling as needed toassure good plant growth until rated. The crop tolerance was rated afterthree to six weeks. The results of these tests are set forth in TableII.

                                      TABLE II                                    __________________________________________________________________________                 Antidote   Injury to plants after                                          Rate                                                                             Cmpd.                                                                             Rate   3 weeks                                                                            4 weeks                                                                             6 weeks                                    Herbicide lb/A                                                                             No. lb/A                                                                             Crop                                                                              %    %     %                                          __________________________________________________________________________    EPTC      6  6   1/16                                                                             Corn                                                                              0    0                                                EPTC      6  6   1/8                                                                              Corn                                                                              0    0     0                                          EPTC      6  6   1/2                                                                              Corn                                                                              0    0     0                                          EPTC      6  6   1  Corn                                                                              0    0     0                                          EPTC      6  6   2  Corn                                                                              0    0     0                                          EPTC      6  6   5  Corn                                                                              0    0     0                                          --        -- 6   5  Corn                                                                              0    0     0                                          EPTC      6  10  1/8                                                                              Corn                                                                              20                                                                              MF                                                  EPTC      6  11  1/8                                                                              Corn                                                                              0                                                     EPTC      6  12  1/8                                                                              Corn                                                                              10                                                                              MF                                                  EPTC      6  13  1/8                                                                              Corn                                                                              60                                                                              MF                                                  EPTC      6  15  1/8                                                                              Corn                                                                              0                                                     EPTC      6  16  1/8                                                                              Corn                                                                              10                                                                              MF                                                  EPTC      6  18  1/8                                                                              Corn                                                                              0                                                     EPTC      6  8   1/2                                                                              Corn     20                                                                              MF                                             EPTC      6  8   2  Corn     0                                                EPTC      6  7   2  Corn     45                                                                              MF                                             EPTC      3  7   4  Corn                                                                              0                                                     EPTC      6  --  -- Corn                                                                              94                                                                              MF 97                                                                              MF  98                                                                              MF                                       S-ethyl diisobutyl                                                                      8  7   2  Corn                                                                              15                                                                              MF                                                  thiocarbamate                                                                 S-ethyl diisobutyl                                                                      8  7   4  Corn                                                                              0                                                     thiocarbamate                                                                 S-ethyl diisobutyl                                                                      8  --  -- Corn                                                                              75                                                                              MF                                                  thiocarbamate                                                                 S-2,3,3-Trichloro-                                                                      1  6   4  Wheat                                                                             20                                                                              ST                                                  allyl-diisopropyl                                                             thiolcarbamate                                                                S-2,3,3-Trichloro-                                                                      1  --  -- Wheat                                                                             90                                                                              MF                                                  allyl-diisopropyl                                                             thiolcarbamate                                                                EPTC +    6 +                                                                 2-chloro-4-ethyl-                                                                       1  6   1/8                                                                              Corn     0                                                amino-6-isopropyl-                                                            amino-s-triazine                                                              EPTC +    6 +                                                                 2-chloro-4-ethyl-                                                                       1  6   2  Corn     0                                                amino-6-isopropyl-                                                            amino-s-triazine                                                              EPTC +    6 +                                                                 2-chloro-4-ethyl-                                                                       1  --  -- Corn     95                                                                              MF                                             amino-6-isopropyl-                                                            amino-s-triazine                                                              EPTC +    6 +                                                                 2-chloro-4,6-bis-                                                                       1  6   1/8                                                                              Corn     0                                                (ethylamino)-s-                                                               triazine                                                                      EPTC +    6 +                                                                 2-chloro-4,6-bis-                                                                       1  6   2  Corn     0                                                (ethylamino)-s-                                                               triazine                                                                      EPTC +    6 +                                                                 2-chloro-4,6-bis-                                                                       1  --  -- Corn     90                                                                              MF                                             (ethylamino)-s-                                                               triazine                                                                      EPTC +    6 +                                                                 2(4-chloro-6-ethyl-                                                                     1  6   1/8                                                                              Corn     0                                                amino-s-triazine-                                                             2-yl-amino)-2-                                                                methylpropionitrile                                                           EPTC +    6 +                                                                 2(4-chloro-6-ethyl-                                                                     1  --  -- Corn     80                                                                              MF                                             amino-s-triazine-                                                             2-yl-amino)-2-                                                                methylpropionitrile                                                           EPTC +    6 +                                                                 2-chloro-4-cyclo-                                                                       1  6   1/8                                                                              Corn     0                                                propylamino-6-                                                                isopropylamino-s-                                                             triazine                                                                      EPTC +    6 +                                                                 2-chloro-4-cyclo-                                                                       1  --  -- Corn     90                                                                              MF,ST                                          propylamino-6-                                                                isopropylamino-s-                                                             triazine                                                                      EPTC +    6 +                                                                 2,4-D     1  6   1/8                                                                              Corn     0                                                EPTC +    6 +                                                                 2,4-D     1  6   2  Corn     10                                                                              ST                                             EPTC +    6 +                                                                 2,4-D     1  --  -- Corn     50                                                                              MF                                             S-propyl dipropyl                                                                       6 +                                                                 thiolcarbamate +                                                              2-chloro-4-ethyl-                                                                       1  6   1/8                                                                              Corn     3 MF                                             amino-6-isopropyl-                                                            amino-s-triazine                                                              S-propyl dipropyl                                                                       6 +                                                                 thiolcarbamate +                                                              2-chloro-4-ethyl-                                                                       1  6   2  Corn     0                                                amino-6-isopropyl-                                                            amino-s-triazine                                                              S-propyl dipropyl                                                                       6 +                                                                 thiolcarbamate +                                                              2-chloro-4-ethyl-                                                                       2  6   1/8                                                                              Corn     0                                                amino-6-isopropyl-                                                            amino-s-triazine                                                              S-propyl dipropyl                                                                       3 +                                                                 thiolcarbamate +                                                              2-chloro-4-ethyl-                                                                       1  6   1/8                                                                              Corn     0                                                amino-6-isopropyl-                                                            amino-s-triazine                                                              S-propyl dipropyl                                                                       3 +                                                                 thiolcarbamate +                                                              2-chloro-4-ethyl-                                                                       1  --  -- Corn     70                                                                              MF                                             amino-6-isopropyl-                                                            amino-s-triazine                                                              S-propyl dipropyl                                                                       6 +                                                                 thiolcarbamate +                                                              2-chloro-4-ethyl-                                                                       1  --  -- Corn     90                                                                              MF                                             amino-6-isopropyl-                                                            amino-s-triazine                                                              S-propyl dipropyl                                                                       6 +                                                                 thiolcarbamate                                                                2-chloro-4,6-bis-                                                                       1  6   1/8                                                                              Corn     3 MF                                             (ethylamino)-s-                                                               triazine                                                                      S-propyl dipropyl                                                                       6 +                                                                 thiolcarbamate +                                                              2-chloro-4,6-bis-                                                                       1  6   2  Corn     0                                                (ethylamino)-s-                                                               triazine                                                                      S-propyl dipropyl                                                                       6 +                                                                 thiolcarbamate +                                                              2-chloro-4,6-bis-                                                                       1  --  -- Corn     70                                                                              MF                                             (ethylamino)-s-                                                               triazine                                                                      S-propyl dipropyl                                                                       6 +                                                                 thiolcarbamate +                                                              2(4-chloro-6-ethyl-                                                                     1  6   1/8                                                                              Corn     0                                                amino-s-triazine-                                                             2-yl-amino)-2-                                                                methylpropionitrile                                                           S-propyl dipropyl                                                                       6 +                                                                 thiolcarbamate +                                                              2(4-chloro-6-ethyl-                                                                     1  --  -- Corn     97                                                                              MF                                             amino-s-triazine-2-                                                           yl-amino)-2-methyl-                                                           propionitrile                                                                 S-propyl dipropyl                                                                       6 +                                                                 thiolcarbamate +                                                              2-chloro-4-cyclo-                                                                       1  6   1/8                                                                              Corn     0                                                propylamino-6-iso-                                                            propylamino-s-                                                                triazine                                                                      S-propyl dipropyl                                                                       6 +                                                                 thiolcarbamate +                                                              2-chloro-4-cyclo-                                                                       1  --  -- Corn     92                                                                              MF                                             propylamino-6-iso-                                                            propylamino-s-                                                                triazine                                                                      S-propyl dipropyl                                                                       6 +                                                                 thiolcarbamate +                                                              2,4-D     1  6   1/8                                                                              Corn     0                                                S-propyl dipropyl                                                                       6 +                                                                 thiolcarbamate +                                                              2,4-D     1  6   2  Corn     0                                                S-propyl dipropyl                                                                       6 +                                                                 thiolcarbamate +                                                              2,4-D     1  --  -- Corn     60                                                                              ST,MF                                          S-propyl dipropyl                                                                       6  6   1/8                                                                              Corn     0                                                thiolcarbamate                                                                S-propyl dipropyl                                                                       6  6   2  Corn     0                                                thiolcarbamate                                                                S-propyl dipropyl                                                                       6  --  -- Corn     90                                                                              MF                                             thiolcarbamate                                                                S-ethyl diisobutyl-                                                                     8 +                                                                 thiolcarbamate +                                                              2-chloro-4-ethyl-                                                                       1  6   1/8                                                                              Corn     0                                                amino-6-isopropyl-                                                            amino-s-triazine                                                              S-ethyl diisobutyl-                                                                     8 +                                                                 thiolcarbamate +                                                              2-chloro-4-ethyl-                                                                       1  6   2  Corn     0                                                amino-6-isopropyl-                                                            amino-s-triazine                                                              S-ethyl diisobutyl                                                                      8 +                                                                 thiolcarbamate +                                                              2-chloro-4-ethyl-                                                                       1  --  -- Corn     0                                                amino-6-isopropyl-                                                            amino-s-triazine                                                              S-ethyl diisobutyl-                                                                     8 +                                                                 thiolcarbamate +                                                              2-chloro-4,6-bis-                                                                       1  6   1/8                                                                              Corn     0                                                (ethylamino)-s-                                                               triazine                                                                      S-ethyl diisobutyl-                                                                     8 +                                                                 thiolcarbamate +                                                              2-chloro-4,6-bis-                                                                       1  6   2  Corn     0                                                (ethylamino)-s-                                                               triazine                                                                      S-ethyl diisobutyl-                                                                     8 +                                                                 thiolcarbamate +                                                              2-chloro-4,6-bis-                                                                       1  --  -- Corn     0                                                (ethylamino)-s-                                                               triazine                                                                      S-ethyl diisobutyl-                                                                     8 +                                                                 thiolcarbamate +                                                              2(4-chloro-6-ethyl-                                                                     1  6   1/8                                                                              Corn     0                                                amino-s-triazine-                                                             2-yl-amino)-2-                                                                methylpropionitrile                                                           S-ethyl diisobutyl-                                                                     8 +                                                                 thiolcarbamate +                                                              2(4-chloro-6-ethyl-                                                                     1  --  -- Corn     20                                                                              MF                                             amino-s-triazine-                                                             2-yl-amino)-2-                                                                methylpropionitrile                                                           S-ethyl diisobutyl-                                                                     8 +                                                                 thiolcarbamate +                                                              2-chloro-4-cyclo-                                                                       1  6   1/8                                                                              Corn     0                                                propylamino-6-iso-                                                            propylamino-s-                                                                triazine                                                                      S-ethyl diisobutyl-                                                                     8 +                                                                 thiolcarbamate +                                                              2-chloro-4-cyclo-                                                                       1  --  -- Corn     10                                                                              MF                                             propylamino-6-iso-                                                            propylamino-s-                                                                triazine                                                                      S-ethyl diisobutyl-                                                                     8 +                                                                 thiolcarbamate +                                                              2,4-D     1  6   1/8                                                                              Corn     0                                                S-ethyl diisobutyl-                                                                     8 +                                                                 thiolcarbamate +                                                              2,4-D     1  6   2  Corn     0                                                S-ethyl diisobutyl-                                                                     8 +                                                                 thiolcarbamate +                                                              2,4-D     1  --  -- Corn       0                                              S-ethyl diisobutyl-                                                                     8  6   1/8                                                                              Corn     0                                                thiolcarbamate                                                                S-ethyl diisobutyl-                                                                     8  6   2  Corn     0                                                thiolcarbamate                                                                S-ethyl diisobutyl-                                                                     8  --  -- Corn     20                                                                              ST                                             thiolcarbamate                                                                S-2,3,3-trichloro-                                                                      8  6   1/8                                                                              Corn     10                                                                              ST                                             allyl-diisopropyl-                                                            thiolcarbamate                                                                S-2,3,3-trichloro-                                                                      8  --  -- Corn     30                                                                              ST                                             allyl-diisopropyl-                                                            thiolcarbamate                                                                S-2,3,3-trichloro-                                                                      3  6   5  Wheat    70                                               allyl-diisopropyl-                                                            thiolcarbamate                                                                S-2,3,3-trichloro-                                                                      3  --  -- Wheat    95                                               allyl-diisopropyl-                                                            thiolcarbamate                                                                S-2,3,3-trichloro-                                                                      3  6   5  Milo     10                                               allyl-diisopropyl-                                                            thiolcarbamate                                                                S-2,3,3-trichloro-                                                                      3  --  -- Milo     90                                               allyl-diisopropyl-                                                            thiolcarbamate                                                                2-chloro-2',6'-                                                                         3  6   5  Milo     20                                               diethyl-N-(methoxy-                                                           methyl) acetanilide                                                           2-chloro-2',6'-                                                                         3  --  -- Milo     70                                               diethyl-N-(methoxy-                                                           methyl) acetanilide                                                           S-ethyl hexahydro-                                                                      3  6   5  Rice     0                                                1H-azepine-1-carbo-                                                           thioate                                                                       S-ethyl hexahydro-                                                                      3  --  -- Rice     20                                               1H-azepine-1-carbo-                                                           thioate                                                                       2-chloro-N-iso-                                                                         3  6   5  Wheat    20                                               propylacetanilide                                                             2-chloro-N-iso-                                                                         3  --  -- Wheat    40                                               propylacetanilide                                                             N,N-diallyl-2-                                                                          4  6   5  Milo     20                                               chloroacetimide                                                               N.N-diallyl-2-                                                                          4  --  -- Milo     70                                               chloroacetamide                                                               S-4-chlorobenzyl-                                                                       6  --  -- Rice     50                                               diethyl thiol-                                                                carbamate                                                                     S-4-chlorobenzyl                                                                        6  6   5  Rice     30                                               diethyl thiol-                                                                carbamate                                                                     S-4-chlorobenzyl                                                                        12 --  -- Rice     90                                               diethyl thiol-                                                                carbamate                                                                     S-4-chlorobenzyl                                                                        12 6   5  Rice     30                                               diethyl thiol-                                                                carbamate                                                                     S-4-chlorobenzyl                                                                        12 --  -- Corn     40                                               diethyl thiol-                                                                carbamate                                                                     S-4-chlorobenzyl                                                                        12 6   5  Corn     0                                                diethyl thiol-                                                                carbamate                                                                     S-ethyl cyclohexyl                                                                      6  6   0.1                                                                              Corn     50                                                                              MF                                             ethyl thiocarbamate                                                           S-ethyl cyclohexyl                                                                      6  --  -- Corn     80                                                                              MF                                             ethyl thiocarbamate                                                           __________________________________________________________________________     EPTC = Sethyl, dipropylthiocarbamate                                          ST = stunting                                                                 MF = malformation                                                        

Test 2: Corn Seed Treatment

Small flats were filled with Felton loamy sand soil. Soil incorporatedherbicides were applied at this time. The soil from each flat was placedinto a five-gallon cement mixer where the soil was mixed as theherbicides were applied as a stock solution in 100 ml. of water. One ml.of stock solution was applied to the soil in a volumetric pipet for eachpound of herbicide desired. One ml. of stock solution contains seven mgof herbicide which equals one pound per acre when applied to soil in8×12×3" flats. After the herbicide incorporation, the soil was placedback into the flats.

Flats of herbicide-treated and untreated soil were then ready to beplanted. A pint sample of soil was then removed from each flat andplaced next to each flat for later use in covering up the seeds. Thesoil was leveled and rows one-half inches deep were made for plantingseeds. Alternating rows of treated and untreated crop seeds were sown.In each test six or more seeds were planted in each row. Rows wereapproximately 11/2" apart in the flat. Seed treatment was applied byplacing 50 mg. of the seed treatment compound with 10 grams of seed in asuitable container and shaking them until the seeds were uniformlycovered with the seed treatment. Seed treatment compounds were appliedas liquid slurries and powder or dust treatments. In some cases acetonewas used to dissolve powdered or solid compounds so they could be moreeffectively applied to the seeds.

After flats were seeded they were covered with the one pint of soilwhich had been removed Just prior to planting. Flats were placed ongreenhouse benches where temperatures ranged from 70°-90° C. Flats werewatered by sprinkling as needed to assure good plant growth. Percentinjury ratings were taken two to four weeks after treatments wereapplied.

In each test, the herbicide is applied alone, in combination with theseed protectant and the seed protectant is applied alone to check forphytotoxicity. The results of these tests are tabulated in Table III.

                                      TABLE III                                   __________________________________________________________________________                                % Injury                                                      Antidote                        Untreated Seed in                          Rate                                                                             Cmpd.                                                                             Treatment Rate                                                                            Treated Seed    Adjacent Row                      Herbicide                                                                              lb/A                                                                             No. % w/w   Crop                                                                              2 weeks 4 weeks 2 weeks                                                                              4 weeks                    __________________________________________________________________________    EPTC     6   1  .5      Corn                                                                              20 MF   60 ST, MF                                 EPTC     6   2  .5      Corn                                                                              10 ST   40 ST, MF                                 EPTC     6   3  .5      Corn                                                                              0       60 ST, MF                                 EPTC     6   4  .5      Corn                                                                              10 ST   70 ST, MF                                 EPTC     6   5  .5      Corn                                                                              0       30 ST, MF                                 EPTC     6   6  .5      Corn                                                                              0       0       0      0                          EPTC     6   7  .5      Corn        30 ST                                     EPTC     6   8  .05     Corn        0                                         EPTC     6   9  .5      Corn                                                                              10 ST           30                                                                              MF                              EPTC     6   10 .5      Corn                                                                              10 ST           5 MF                              EPTC     6   11 .5      Corn                                                                              10 ST           10                                                                              MF                              EPTC     6    12                                                                              .5      Corn                                                                              100                                                                              IG           5 MF                              EPTC     6   13 .5      Corn                                                                              100                                                                              IG           15                                                                              MF                              EPTC     6   14 .5      Corn                                                                              10 ST           50                                                                              MF                              EPTC     6   15 .5      Corn                                                                              100                                                                              IG           5 ST                              EPTC     6   16 .5      Corn                                                                              10 ST           5 ST                              EPTC     6   17 .5      Corn                                                                              20 ST           35                                                                              MF                              EPTC     6   18 .5      Corn                                                                              0               5 ST                              EPTC     6   19 .5      Corn                                                                              0               50                                                                              MF                              EPTC     6   20 .5      Corn                                                                              10 ST   10 ST   30                                                                              MF   65                                                                              MF                       EPTC     6   21 .5      Corn                                                                              0       0       10                                                                              MF   55                                                                              MF                       EPTC     6   22 .5      Corn                                                                              60 MF   70 MF   85                                                                              MF   80                                                                              MF                       EPTC     6   23 .5      Corn                                                                              20 MF   40 MF   85                                                                              MF   80                                                                              MF                       EPTC     6   24 .5      Corn                                                                              10 ST   10 ST   75                                                                              MF   80                                                                              MF                       EPTC     6   25 .5      Corn                                                                              0       30 MF   60                                                                              MF   60                                                                              MF                       EPTC     6   26 .5      Corn                                                                              0       10 MF   83                                                                              MF   80                                                                              MF                       EPTC     6   27 .5      Corn                                                                              70 MF           60                                                                              MF                              EPTC     6   28 .5      Corn                                                                              30 ST, MF       75                                                                              MF                              EPTC     6   29 .5      Corn                                                                              60 MF           70                                                                              MF                              EPTC     6   30 .5      Corn                                                                              60 MF           70                                                                              MF                              EPTC     6   31 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6   32 .5      Corn                                                                              60 MF           75                                                                              MF                              EPTC     6   33 .5      Corn                                                                              50 ST, MF       75                                                                              MF                              EPTC     6   34 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6   35 .5      Corn                                                                              50 MF           75                                                                              MF                              EPTC     6   36 .5      Corn                                                                              60 MF           85                                                                              MF                              EPTC     6   37 .5      Corn                                                                              40 ST, MF       85                                                                              MF                              EPTC     6   38 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6   39 .5      Corn                                                                              60 MF           70                                                                              MF                              EPTC     6   40 .5      Corn                                                                              50 MF           80                                                                              MF                              EPTC     6   41 .5      Corn                                                                              10 ST, MF                                                                             50 MF   75                                                                              MF   65                                                                              MF                       EPTC     6   42 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6   43 .5      Corn                                                                              10 ST, MF                                                                             50 MF   85                                                                              MF   80                                                                              MF                       EPTC     6   44 .5      Corn                                                                              40 MF           70                                                                              MF                              EPTC     6   45 .5      Corn                                                                              60 MF           85                                                                              MF                              EPTC     6   46 .5      Corn                                                                              40 ST, MF       85                                                                              MF                              EPTC     6   47 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6   48 .5      Corn                                                                              50 ST, MF       80                                                                              MF                              EPTC     6   49 .5      Corn                                                                              60 MF           70                                                                              MF                              EPTC     6   50 .5      Corn                                                                              60 MF           90                                                                              MF                              EPTC     6   51 .5      Corn                                                                              60 MF           70                                                                              MF                              EPTC     6   52 .5      Corn                                                                              60 ST, MF       80                                                                              MF                              EPTC     6   53 .5      Corn                                                                              50 MF           70                                                                              MF                              EPTC     6   54 .5      Corn                                                                              60 MF           70                                                                              MF                              EPTC     6   55 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6   56 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6   57 .5      Corn                                                                              60 MF           65                                                                              MF                              EPTC     6   58 .5      Corn                                                                              50 MF           75                                                                              MF                              EPTC     6   59 .5      Corn                                                                              60 ST, MF       80                                                                              MF                              EPTC     6   60 .5      Corn                                                                              60 ST, MF       75                                                                              MF                              EPTC     6   61 .5      Corn                                                                              60 MF           85                                                                              MF                              EPTC     6   62 .5      Corn                                                                              40 ST, MF                                                                             60 MF   80                                                                              MF   70                                                                              MF                       EPTC     6   63 .5      Corn                                                                              30 ST, MF                                                                             60 MF   70                                                                              MF   70                                                                              MF                       EPTC     6   64 .5      Corn                                                                              30 ST, MF                                                                             50 MF   65                                                                              MF   70                                                                              MF                       EPTC     6   65 .5      Corn                                                                              60 ST, MF                                                                             70 MF   75                                                                              MF   80                                                                              MF                       EPTC     6   66 .5      Corn                                                                              50 ST, MF       70                                                                              MF                              EPTC     6   67 .5      Corn                                                                              40 ST, MF       80                                                                              MF                              EPTC     6   68 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6   69 .5      Corn                                                                              20 ST, MF                                                                             50 MF   70                                                                              MF   70                                                                              MF                       EPTC     6   70 .5      Corn                                                                              40 ST, MF                                                                             50 ST, MF                                                                             80                                                                              MF   80                                                                              MF                       EPTC     6   71 .5      Corn                                                                              40 ST, MF       80                                                                              MF                              EPTC     6   72 .5      Corn                                                                              60 MF           65                                                                              MF                              EPTC     6   73 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6   74 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6   75 .5      Corn                                                                              60 ST, MF       80                                                                              MF                              EPTC     6   76 .5      Corn                                                                              50 ST, MF       75                                                                              MF                              EPTC     6   77 .5      Corn                                                                              60 MF           75                                                                              MF                              EPTC     6   78 .5      Corn                                                                              60 ST, MF       75                                                                              MF                              EPTC     6   79 .5      Corn                                                                              50 ST, MF       75                                                                              MF                              EPTC     6   80 .5      Corn                                                                              60 MF   60 MF   65                                                                              MF   70                                                                              MF                       EPTC     6   81 .5      Corn                                                                              10 ST   20 MF   50                                                                              MF   50                                                                              MF                       EPTC     6   82 .5      Corn                                                                              30 ST   30 ST   50                                                                              MF   50                                                                              MF                       EPTC     6   83 .5      Corn                                                                              20 ST   20 ST   20                                                                              MF   25                                                                              MF                       EPTC     6   84 .5      Corn                                                                              10 ST   10 ST   15                                                                              MF   20                                                                              MF                       EPTC     6   85 .5      Corn                                                                              30 ST   10 ST   35                                                                              MF   45                                                                              MF                       EPTC     6   86 .5      Corn                                                                              50 ST, MF       75                                                                              MF                              EPTC     6   87 .5      Corn                                                                              30 ST, MF       75                                                                              MF                              EPTC     6   88 .5      Corn                                                                              50 ST, MF       70                                                                              MF                              EPTC     6   89 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6   90 .5      Corn                                                                              20 ST, MF                                                                             30 ST, MF                                                                             80                                                                              MF   80                                                                              MF                       EPTC     6   91 .5      Corn                                                                              40 ST, MF       80                                                                              MF                              EPTC     6   92 .5      Corn                                                                              50 ST, MF       80                                                                              MF                              EPTC     6   93 .5      Corn                                                                              60 ST   20 ST   75                                                                              MF   75                                                                              MF                       EPTC     6   94 .5      Corn                                                                              30 ST, MF       80                                                                              MF                              EPTC     6   95 .5      Corn                                                                              100                                                                              IG           90                                                                              MF                              EPTC     6   96 .5      Corn                                                                              30 ST, MF       80                                                                              MF                              EPTC     6   97 .5      Corn                                                                              30 ST, MF       75                                                                              MF                              EPTC     6   98 .5      Corn                                                                              60 ST, MF       75                                                                              MF                              EPTC     6   99 .5      Corn                                                                              30 ST   30 ST, MF                                                                             85                                                                              MF   80                                                                              MF                       EPTC     6  100 .5      Corn                                                                              40 ST, MF       65                                                                              MF                              EPTC     6  101 .5      Corn                                                                              50 ST, MF       75                                                                              MF                              EPTC     6  102 .5      Corn                                                                              30 ST, MF                                                                             50 MF   85                                                                              MF   80                                                                              MF                       EPTC     6  103 .5      Corn                                                                              50 MF           80                                                                              MF                              EPTC     6  104 .5      Corn                                                                              40 ST, MF       85                                                                              MF                              EPTC     6  105 .5      Corn                                                                              50 ST, MF       85                                                                              MF                              EPTC     6  106 .5      Corn                                                                              40 ST, MF       80                                                                              MF                              EPTC     6  107 .5      Corn                                                                              30 ST   20 ST, MF                                                                             85                                                                              MF   80                                                                              MF                       EPTC     6  108 .5      Corn                                                                              40 ST, MF       90                                                                              MF                              EPTC     6  109 .5      Corn                                                                              30 ST, MF       90                                                                              MF                              EPTC     6  110 .5      Corn                                                                              40 ST, MF       85                                                                              MF                              EPTC     6  111 .5      Corn                                                                              40 ST, MF       75                                                                              MF                              EPTC     6  112 .5      Corn                                                                              60 ST, IG                                                                             30 MF   85                                                                              MF                              EPTC     6  113 .5      Corn                                                                              30 ST, MF       80                                                                              MF                              EPTC     6  114 .5      Corn                                                                              30 ST, MF       80                                                                              MF                              EPTC     6  115 .5      Corn                                                                              40 ST, MF       90                                                                              MF                              EPTC     6  116 .5      Corn                                                                              30 ST   30 ST, MF                                                                             75                                                                              MF   80                                                                              MF                       EPTC     6  117 .5      Corn                                                                              20 ST, MF       70                                                                              MF                              EPTC     6  118 .5      Corn                                                                              30 ST, MF       70                                                                              MF                              EPTC     6  119 .5      Corn                                                                              30 ST, MF       70                                                                              MF                              EPTC     6  120 .5      Corn                                                                              30 ST, MF       75                                                                              MF                              EPTC     6  121 .5      Corn                                                                              40 ST, MF       75                                                                              MF                              EPTC     6  122 .5      Corn                                                                              20 ST, MF       35                                                                              MF                              EPTC     6  123 .5      Corn                                                                              20 ST   20 ST   10                                                                              MF   20                                                                              MF                       EPTC     6  124 .5      Corn                                                                              30 ST, MF       75                                                                              MF                              EPTC     6  125 .5      Corn                                                                              40 ST, MF       80                                                                              MF                              EPTC     6  126 .5      Corn                                                                              40 ST, MF       80                                                                              MF                              EPTC     6  127 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6  128 .5      Corn                                                                              50 MF           55                                                                              MF                              EPTC     6  129 .5      Corn                                                                              30 ST, LB                                                                             30 ST, LB                                                                             50                                                                              MF   60                                                                              MF                       EPTC     6  130 .5      Corn                                                                              30 ST   30 ST   40                                                                              MF   60                                                                              MF                       EPTC     6  131 .5      Corn                                                                              10 ST   0       25                                                                              MF   55                                                                              MF                       EPTC     6  132 .5      Corn                                                                              0       0       45                                                                              MF   55                                                                              MF                       EPTC     6  133 .5      Corn                                                                              40 MF           65                                                                              MF                              EPTC     6  134 .5      Corn                                                                              30 ST, MF       70                                                                              MF                              EPTC     6  135 .5      Corn                                                                              40 ST, MF       70                                                                              MF                              EPTC     6  136 .5      Corn                                                                              50 ST, MF       80                                                                              MF                              EPTC     6  137 .5      Corn                                                                              30 ST, MF       85                                                                              MF                              EPTC     6  138 .5      Corn                                                                              30 ST, MF       75                                                                              MF                              EPTC     6  139 .5      Corn                                                                              50 ST, MF       80                                                                              MF                              EPTC     6  140 .5      Corn                                                                              50 ST, MF       75                                                                              MF                              EPTC     6  141 .5      Corn                                                                              20 ST, MF                                                                             30 ST, MF                                                                             80                                                                              MF   80                                                                              MF                       EPTC     6  142 .5      Corn                                                                              20 ST, MF                                                                             50 MF   75                                                                              MF   70                                                                              MF                       EPTC     6  143 .5      Corn                                                                              10 ST, MF                                                                             50 MF   85                                                                              MF   80                                                                              MF                       EPTC     6  144 .5      Corn                                                                              50 ST, MF       85                                                                              MF                              EPTC     6  145 .5      Corn                                                                              20 ST, MF       80                                                                              MF                              EPTC     6  146 .5      Corn                                                                              20 ST, MF                                                                             20 ST, MF                                                                             65                                                                              MF   70                                                                              MF                       EPTC     6  147 .5      Corn                                                                              10 ST   0       75                                                                              MF   80                                                                              MF                       EPTC     6  148 .5      Corn                                                                              60 MF           75                                                                              MF                              EPTC     6  149 .5      Corn                                                                              40 ST, MF       75                                                                              MF                              EPTC     6  150 .5      Corn                                                                              50 ST, MF       70                                                                              MF                              EPTC     6  151 .5      Corn                                                                              50 MF           70                                                                              MF                              EPTC     6  152 .5      Corn                                                                              40 MF           80                                                                              MF                              EPTC     6  153 .5      Corn                                                                              50 MF           85                                                                              MF                              EPTC     6  154 .5      Corn                                                                              30 ST, MF       75                                                                              MF                              EPTC     6  155 .5      Corn                                                                              20 ST, MF                                                                             40 MF   85                                                                              MF   80                                                                              MF                       EPTC     6  156 .5      Corn                                                                              60 MF           85                                                                              MF                              EPTC     6  157 .5      Corn                                                                              50 ST, MF       80                                                                              MF                              EPTC     6  158 .5      Corn                                                                              20 ST, MF       70                                                                              MF                              EPTC     6  159 .5      Corn                                                                              30 ST, MF       75                                                                              MF                              EPTC     6  160 .5      Corn                                                                              50 ST, MF       75                                                                              MF                              EPTC     6  161 .5      Corn                                                                              50 ST, MF       70                                                                              MF                              EPTC     6  162 .5      Corn                                                                              30 ST, MF       65                                                                              MF                              EPTC     6  163 .5      Corn                                                                              60 ST, MF       60                                                                              MF                              EPTC     6  164 .5      Corn                                                                              60 MF           70                                                                              MF                              EPTC     6  165 .5      Corn                                                                              60 MF           75                                                                              MF                              EPTC     6  166 .5      Corn                                                                              40 ST, MF                                                                             60 MF   75                                                                              MF   60                                                                              MF                       EPTC     6  167 .5      Corn                                                                              50 ST, MF       75                                                                              MF                              EPTC     6  168 .5      Corn                                                                              60 ST, MF       80                                                                              MF                              EPTC     6  169 .5      Corn                                                                              30 ST   30 ST   80                                                                              MF   80                                                                              MF                       EPTC     6  170 .5      Corn                                                                              30 ST, MF       80                                                                              MF                              EPTC     6  171 .5      Corn                                                                              60 MF           75                                                                              MF                              EPTC     6  172 .5      Corn                                                                              40 MF           75                                                                              MF                              EPTC     6  173 .5      Corn                                                                              30 ST, MF                                                                             50 MF   80                                                                              MF   80                                                                              MF                       EPTC     6  174 .5      Corn                                                                              60 ST, MF       80                                                                              MF                              EPTC     6  175 .5      Corn                                                                              30 ST, MF       85                                                                              MF                              EPTC     6  176 .5      Corn                                                                              40 ST, MF       85                                                                              MF                              EPTC     6  177 .5      Corn                                                                              30 ST, MF       85                                                                              MF                              EPTC     6  178 .5      Corn                                                                              50 ST, MF       80                                                                              MF                              EPTC     6  179 .5      Corn                                                                              0       0       0      5 MF                       EPTC     6  180 .5      Corn                                                                              0       0       0      0                          EPTC     6  181 .5      Corn                                                                              0       0       0      0                          EPTC     6  182 .5      Corn                                                                              0       0       0      0                          EPTC     6  183 .5      Corn                                                                              0       0       0      0                          EPTC     6  184 .5      Corn                                                                              0       0       5 MF   15                                                                              MF                       EPTC     6  185 .5      Corn                                                                              0       0       3 MF   30                                                                              MF                       EPTC     6  186 .5      Corn                                                                              0       0       0      0                          EPTC     6  187 .5      Corn                                                                              0       0       5 MF   45                                                                              MF                       EPTC     6  188 .5      Corn                                                                              0       0       13                                                                              MF   45                                                                              MF                       EPTC     6  189 .5      Corn                                                                              0       0       5 MF   35                                                                              MF                       EPTC     6  190 .5      Corn                                                                              0       0       0      15                                                                              MF                       EPTC     6  191 .5      Corn                                                                              0       0       3 MF   50                                                                              MF                       EPTC     6  192 .5      Corn                                                                              0       0       5 MF   40                                                                              MF                       EPTC     6  193 .5      Corn                                                                              0       0       10                                                                              MF   35                                                                              MF                       EPTC     6  194 .5      Corn                                                                              0       0       0      25                                                                              MF                       EPTC     6  195 .5      Corn                                                                              30 ST, MF       55                                                                              MF                              EPTC     6  196 .5      Corn                                                                              100                                                                              IG           55                                                                              MF                              EPTC     6  197 .5      Corn                                                                              60 MF           75                                                                              MF                              EPTC     6  198 .5      Corn                                                                              30 ST, MF                                                                             30 MF   75                                                                              MF   80                                                                              MF                       EPTC     6  199 .5      Corn                                                                              50 ST, MF       80                                                                              MF                              EPTC     6  200 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6  201 .5      Corn                                                                              40 ST, MF       88                                                                              MF                              EPTC     6  202 .5      Corn                                                                              50 MF           60                                                                              MF                              EPTC     6  203 .5      Corn                                                                              50 MF           65                                                                              MF                              EPTC     6  204 .5      Corn                                                                              20 ST   10 ST   55                                                                              MF   50                                                                              MF                       EPTC     6  205 .5      Corn                                                                              30 ST, MF       65                                                                              MF                              EPTC     6  206 .5      Corn                                                                              20 ST, MF                                                                             20 ST, MF                                                                             40                                                                              MF   55                                                                              MF                       EPTC     6  207 .5      Corn                                                                              100                                                                              IG           55                                                                              MF                              EPTC     6  208 .5      Corn                                                                              60 ST, MF       70                                                                              MF                              EPTC     6  209 .5      Corn                                                                              0       0       30                                                                              MF   40                                                                              MF                       EPTC     6  210 .5      Corn                                                                              0       10 ST   5 MF   35                                                                              MF                       EPTC     6  211 .5      Corn                                                                              0       0       25                                                                              MF   50                                                                              MF                       EPTC     6  212 .5      Corn                                                                              0       10 ST   18                                                                              MF   50                                                                              MF                       EPTC     6  213 .5      Corn                                                                              50 ST   30 ST   70                                                                              MF   70                                                                              MF                       EPTC     6  214 .5      Corn                                                                              0       10 ST   50                                                                              MF   65                                                                              MF                       EPTC     6  215 .5      Corn                                                                              10 ST   0       85                                                                              MF   70                                                                              MF                       EPTC     6  216 .5      Corn                                                                              10 ST   10 ST, MF                                                                             95                                                                              MF   90                                                                              MF                       EPTC     6  217 .5      Corn                                                                              100                                                                              IG   100                                                                              IG   30                                                                              MF   45                                                                              MF                       EPTC     6  218 .5      Corn                                                                              10 ST   10 ST   20                                                                              MF   15                                                                              MF                       EPTC     6  219 .5      Corn                                                                              100                                                                              IG           45                                                                              MF                              EPTC     6  220 .5      Corn                                                                              0       10 ST   0      0                          EPTC     6  221 .5      Corn                                                                              0       10 ST   15                                                                              MF   35                                                                              MF                       EPTC     6  222 .5      Corn                                                                              100                                                                              IG           50                                                                              MF                              EPTC     6  223 .5      Corn                                                                              10 ST   20 ST   70                                                                              MF   70                                                                              MF                       EPTC     6  224 .5      Corn                                                                              50 ST   30 ST   45                                                                              MF   80                                                                              MF                       EPTC     6  225 .5      Corn                                                                              30 ST   30 ST   70                                                                              MF   80                                                                              MF                       EPTC     6  226 .5      Corn                                                                              20 ST   10 ST   93                                                                              MF   80                                                                              MF                       EPTC     6  227 .5      Corn                                                                              20 ST   20 ST   85                                                                              MF   80                                                                              MF                       EPTC     6  228 .5      Corn                                                                              40 ST, MF       93                                                                              MF                              EPTC     6  229 .5      Corn                                                                              40 ST, MF       90                                                                              MF                              EPTC     6  230 .5      Corn                                                                              40 ST, MF       95                                                                              MF                              EPTC     6  231 .5      Corn                                                                              40 ST, MF       88                                                                              MF                              EPTC     6  232 .5      Corn                                                                              0       0       55                                                                              MF   60                                                                              MF                       EPTC     6  233 .5      Corn                                                                              30 ST, MF       70                                                                              MF                              EPTC     6  234 .5      Corn                                                                              0       10 ST   55                                                                              MF   60                                                                              MF                       EPTC     6  235 .5      Corn                                                                              10 ST   10 ST   70                                                                              MF   65                                                                              MF                       EPTC     6  236 .5      Corn                                                                              0       0       30                                                                              MF   45                                                                              MF                       EPTC     6  237 .5      Corn                                                                              0       10 ST   65                                                                              MF   65                                                                              MF                       EPTC     6  238 .5      Corn                                                                              30 ST, MF       75                                                                              MF                              EPTC     6  239 .5      Corn                                                                              50 ST, MF       80                                                                              MF                              EPTC     6  240 .5      Corn                                                                              0       10 MF   25                                                                              MF   55                                                                              MF                       EPTC     6  241 .5      Corn                                                                              0       0       45                                                                              MF   45                                                                              MF                       EPTC     6  242 .5      Corn                                                                              30 ST, MF       50                                                                              MF                              EPTC     6  243 .5      Corn                                                                              10 ST, MF                                                                             30 MF   75                                                                              MF   70                                                                              MF                       EPTC     6  244 .5      Corn                                                                              0               20                                                                              MF                              EPTC     6  245 .5      Corn                                                                              10 ST           28                                                                              MF                              EPTC     6  246 .5      Corn                                                                              0               8 MF                              EPTC     6  247 .5      Corn                                                                              10 ST           3 MF                              EPTC     6  248 .5      Corn                                                                              20 ST           70                                                                              MF                              EPTC     6  249 .5      Corn                                                                              10 ST           70                                                                              MF                              EPTC     6  250 .5      Corn                                                                              0               65                                                                              MF                              EPTC     6  251 .5      Corn                                                                              0               20                                                                              MF                              EPTC     6  252 .5      Corn                                                                              0               15                                                                              MF                              EPTC     6  253 .5      Corn                                                                              0               8 MF                              EPTC     6  254 .5      Corn                                                                              5  MF           50                                                                              MF                              EPTC     6  255 .5      Corn                                                                              0               5 MF                              EPTC     6  256 .5      Corn                                                                              0               15                                                                              MF                              EPTC     6  257 .5      Corn                                                                              0               70                                                                              MF                              EPTC     6  258 .5      Corn                                                                              0               10                                                                              MF                              EPTC     6  259 .5      Corn                                                                              0               35                                                                              MF                              EPTC     6  260 .5      Corn                                                                              0               15                                                                              MF                              EPTC     6  261 .5      Corn                                                                              0               5 MF                              EPTC     6  262 .5      Corn                                                                              0               55                                                                              MF                              EPTC     6  263 .5      Corn                                                                              10 MF           60                                                                              MF                              EPTC     6  264 .5      Corn                                                                              0               15                                                                              MF                              EPTC     6  265 .5      Corn                                                                              0               70                                                                              MF                              EPTC     6  266 .5      Corn                                                                              0               50                                                                              MF                              EPTC     6  267 .5      Corn                                                                              0               45                                                                              MF                              EPTC     6  268 .5      Corn                                                                              0               3 MF                              EPTC     6  269 .5      Corn                                                                              0               35                                                                              MF                              EPTC     6  270 .5      Corn                                                                              0               33                                                                              MF                              EPTC     6  271 .5      Corn                                                                              0               20                                                                              MF                              EPTC     6  272 .5      Corn                                                                              0               40                                                                              MF                              EPTC     6  273 .5      Corn                                                                              0               45                                                                              MF                              EPTC     6  274 .5      Corn                                                                              0               35                                                                              MF                              EPTC     6  275 .5      Corn                                                                              0               40                                                                              MF                              EPTC     6  276 .5      Corn                                                                              0               40                                                                              MF                              EPTC     6  277 .5      Corn                                                                              10 ST           35                                                                              MF                              EPTC     6  278 .5      Corn                                                                              0               40                                                                              MF                              EPTC     6  279 .5      Corn                                                                              0               33                                                                              MF                              EPTC     6  280 .5      Corn                                                                              0               50                                                                              MF                              EPTC     6  281 .5      Corn                                                                              0               65                                                                              MF                              EPTC     6  282 .5      Corn                                                                              10 LB           38                                                                              MF                              EPTC     6  283 .5      Corn                                                                              0               80                                                                              MF                              EPTC     6  284 .5      Corn                                                                              0               35                                                                              MF                              EPTC     6  285 .5      Corn                                                                              0               75                                                                              MF                              EPTC     6  286 .5      Corn                                                                              10 ST           70                                                                              MF                              EPTC     6  287 .5      Corn                                                                              10 ST           75                                                                              MF                              EPTC     6  288 .5      Corn                                                                              10 ST           35                                                                              MF                              EPTC     6  289 .5      Corn                                                                              0               35                                                                              MF                              EPTC     6  290 .5      Corn                                                                              0               50                                                                              MF                              EPTC     6  291 .5      Corn                                                                              0               50                                                                              MF                              EPTC     6  292 .5      Corn                                                                              0               30                                                                              MF                              EPTC     6  293 .5      Corn                                                                              0               55                                                                              MF                              EPTC     6  294 .5      Corn                                                                              0               60                                                                              MF                              EPTC     6  295 .5      Corn                                                                              0               25                                                                              MF                              EPTC     6  296 .5      Corn                                                                              0               15                                                                              MF                              EPTC     6  297 .5      Corn                                                                              0               10                                                                              MF                              EPTC     6  298 .5      Corn                                                                              0               5 MF                              EPTC     6  299 .5      Corn                                                                              0               20                                                                              MF                              EPTC     6  300 .5      Corn                                                                              0               0                                 EPTC     6  301 .5      Corn                                                                              0               23                                                                              MF                              EPTC     6  302 .5      Corn                                                                              0               25                                                                              MF                              EPTC     6  303 .5      Corn                                                                              0               15                                                                              MF                              EPTC     6  304 .5      Corn                                                                              0               40                                                                              MF                              EPTC     6  305 .5      Corn                                                                              0               35                                                                              MF                              EPTC     6  306 .5      Corn                                                                              0               15                                                                              MF                              EPTC     6  307 .5      Corn                                                                              0               15                                                                              MF                              EPTC     6  308 .5      Corn                                                                              0               8 MF                              EPTC     6  309 .5      Corn                                                                              0               25                                                                              MF                              EPTC     6  310 .5      Corn                                                                              0               45                                                                              MF                              EPTC     6  311 .5      Corn                                                                              0               30                                                                              MF                              EPTC     6  312 .5      Corn                                                                              0               70                                                                              MF                              EPTC     6  313 .5      Corn                                                                              0               65                                                                              MF                              EPTC     6  314 .5      Corn                                                                              30 ST, MF       60                                                                              MF                              EPTC     6  315 .5      Corn                                                                              50 MF           70                                                                              MF                              EPTC     6  316 .5      Corn                                                                              0               0                                 EPTC     6  317 .5      Corn                                                                              0               70                                                                              MF                              EPTC     6  318 .5      Corn                                                                              30 ST, MF       60                                                                              MF                              EPTC     6  319 .5      Corn                                                                              50 ST, MF       60                                                                              MF                              EPTC     6  320 .5      Corn                                                                              0               0                                 EPTC     6  321 .5      Corn                                                                              0               65                                                                              MF                              EPTC     6  322 .5      Corn                                                                              10 ST           10                                                                              MF                              EPTC     6  323 .5      Corn                                                                              10 ST           40                                                                              MF                              EPTC     6  324 .5      Corn                                                                              60 MF           75                                                                              MF                              EPTC     6  325 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6  326 .5      Corn                                                                              20 ST           70                                                                              MF                              EPTC     6  327 .5      Corn                                                                              30 ST, MF       75                                                                              MF                              EPTC     6  328 .5      Corn                                                                              60 ST, MF       75                                                                              MF                              EPTC     6  329 .5      Corn                                                                              0               60                                                                              MF                              EPTC     6  330 .5      Corn                                                                              30 ST, MF       65                                                                              MF                              EPTC     6  331 .5      Corn                                                                              10 ST           70                                                                              MF                              EPTC     6  332 .5      Corn                                                                              0               5 MF                              EPTC     6  333 .5      Corn                                                                              0               15                                                                              MF                              EPTC     6  334 .5      Corn                                                                              0               23                                                                              MF                              EPTC     6  335 .5      Corn                                                                              20 ST, LB       35                                                                              MF                              EPTC     6  336 .5      Corn                                                                              95 ST           30                                                                              MF                              EPTC     6  337 .5      Corn                                                                              0               5 MF                              EPTC     6  338 .5      Corn                                                                              0               60                                                                              MF                              EPTC     6  339 .5      Corn                                                                              30 MF           75                                                                              MF                              EPTC     6  340 .5      Corn                                                                              0               25                                                                              MF                              EPTC     6  341 .5      Corn                                                                              0               30                                                                              MF                              EPTC     6  342 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6  343 .5      Corn                                                                              0               45                                                                              MF                              EPTC     6  344 .5      Corn                                                                              10 ST           75                                                                              MF                              EPTC     6  345 .5      Corn                                                                              0               75                                                                              MF                              EPTC     6  346 .5      Corn                                                                              10 ST           65                                                                              MF                              EPTC     6  347 .5      Corn                                                                              50 ST, MF       80                                                                              MF                              EPTC     6  348 .5      Corn                                                                              0               65                                                                              MF                              EPTC     6  349 .5      Corn                                                                              60 ST, MF       75                                                                              MF                              EPTC     6  350 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6  351 .5      Corn                                                                              60 ST, MF       75                                                                              MF                              EPTC     6  352 .5      Corn                                                                              60 ST, MF       80                                                                              MF                              EPTC     6  353 .5      Corn                                                                              60 ST, MF       75                                                                              MF                              EPTC     6  354 .5      Corn                                                                              50 ST, MF       80                                                                              MF                              EPTC     6  355 .5      Corn                                                                              60 ST, MF       70                                                                              MF                              EPTC     6  356 .5      Corn                                                                              50 ST, LB       70                                                                              MF                              EPTC     6  357 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6  358 .5      Corn                                                                              30 ST           75                                                                              MF                              EPTC     6  359 .5      Corn                                                                              30 ST, MF       75                                                                              MF                              EPTC     6  360 .5      Corn                                                                              50 ST, MF       70                                                                              MF                              EPTC     6  361 .5      Corn                                                                              50 ST, MF       75                                                                              MF                              EPTC     6  362 .5      Corn                                                                              30 ST           75                                                                              MF                              EPTC     6  363 .5      Corn                                                                              30 ST, MF       80                                                                              MF                              EPTC     6  364 .5      Corn                                                                              10 ST           55                                                                              MF                              EPTC     6  365 .5      Corn                                                                              50 ST, MF       65                                                                              MF                              EPTC     6  366 .5      Corn                                                                              0               65                                                                              MF                              EPTC     6  367 .5      Corn                                                                              0               75                                                                              MF                              EPTC     6  368 .5      Corn                                                                              0               30                                                                              MF                              EPTC     6  369 .5      Corn                                                                              0               25                                                                              MF                              EPTC     6  370 .5      Corn                                                                              70 LB   70 MF   80                                                                              MF   80                                                                              MF                       EPTC     6  371 .5      Corn                                                                              40 ST   50 MF   85                                                                              MF   80                                                                              MF                       EPTC     6  372 .5      Corn                                                                              30 ST   40 ST, MF                                                                             80                                                                              MF   80                                                                              MF                       EPTC     6  373 .5      Corn                                                                              30 ST, MF,      75                                                                              MF                                                             LB                                             EPTC     6  374 .5      Corn                                                                              60 MF           85                                                                              MF                              EPTC     6  375 .5      Corn                                                                              50 ST, LB                                                                             30 MF   90                                                                              MF   80                                                                              MF                       EPTC     6  376 .5      Corn                                                                              50 MF           90                                                                              MF                              EPTC     6  377 .5      Corn                                                                              40 ST, MF       70                                                                              MF                              EPTC     6  378 .5      Corn                                                                              80 MF                                             EPTC     6  379 .5      Corn                                                                              50 MF           85                                                                              MF                              EPTC     6  380 .5      Corn                                                                              10 ST   20 MF   90                                                                              MF   80                                                                              MF                       EPTC     6  381 .5      Corn                                                                              30 ST   40 MF   85                                                                              MF   80                                                                              MF                       EPTC     6  382 .5      Corn                                                                              50 MF           80                                                                              MF                              EPTC     6  383 .5      Corn                                                                              50 ST, LB                                                                             30 ST   90                                                                              MF   80                                                                              MF                       EPTC     6  384 .5      Corn                                                                              20 ST   10 ST   70                                                                              MF   80                                                                              MF                       EPTC     6  385 .5      Corn                                                                              60 MF           85                                                                              MF                              EPTC     6  386 .5      Corn                                                                              10 ST   30 MF   75                                                                              MF                              EPTC     6  387 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6  388 .5      Corn                                                                              100                                                                              IG           55                                                                              MF                              EPTC     6  389 .5      Corn                                                                              10 ST   0       75                                                                              MF                              EPTC     6  390 .5      Corn                                                                              15 ST, MF       80                                                                              MF                              EPTC     6  391 .5      Corn                                                                              10 ST   0       80                                                                              MF                              EPTC     6  392 .5      Corn                                                                              60 ST, MF       75                                                                              MF                              EPTC     6  393 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6  394 .5      Corn                                                                              50 ST, MF       80                                                                              MF                              EPTC     6  395 .5      Corn                                                                              10 ST   10 MF   65                                                                              MF                              EPTC     6  396 .5      Corn                                                                              10 ST   0       75                                                                              MF                              EPTC     6  397 .5      Corn                                                                              10 ST   20 MF   60                                                                              MF                              EPTC     6  398 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6  399 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6  400 .5      Corn                                                                              60 MF           75                                                                              MF                              EPTC     6  401 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6  402 .5      Corn                                                                              40 ST, MF       75                                                                              MF                              EPTC     6  403 .5      Corn                                                                              60 ST, MF       80                                                                              MF                              EPTC     6  404 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  405 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  406 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  407 .5      COrn                                                                              70 MF           80                                                                              MF                              EPTC     6  408 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  409 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  410 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  411 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6  412 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  413 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  414 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  415 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  416 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  417 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6  418 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  419 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  420 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  421 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  422 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  423 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  424 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  425 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  426 .5      Corn                                                                              60 ST, MF       75                                                                              MF                              EPTC     6  427 .5      Corn                                                                              70 MF           75                                                                              MF                              EPTC     6  428 .5      Corn                                                                              70 MF           75                                                                              MF                              EPTC     6  429 .5      Corn                                                                              70 ST, MF       80                                                                              MF                              EPTC     6  430 .5      Corn                                                                              70 ST, MF       75                                                                              MF                              EPTC     6  431 .5      Corn                                                                              70 ST, MF       80                                                                              MF                              EPTC     6  432 .5      Corn                                                                              70 ST, MF       80                                                                              MF                              EPTC     6  433 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  434 .5      Corn                                                                              70 ST, MF       80                                                                              MF                              EPTC     6  435 .5      Corn                                                                              70 MF           75                                                                              MF                              EPTC     6  436 .5      Corn                                                                              60 ST, MF       75                                                                              MF                              EPTC     6  437 .5      Corn                                                                              50 ST, MF       75                                                                              MF                              EPTC     6  438 .5      Corn                                                                              70 ST, MF       80                                                                              MF                              EPTC     6  439 .5      Corn                                                                              20 ST           75                                                                              MF                              EPTC     6  440 .5      Corn                                                                              10 ST           65                                                                              MF                              EPTC     6  441 .5      Corn                                                                              30 ST           75                                                                              MF                              EPTC     6  442 .5      Corn                                                                              10 ST           70                                                                              MF                              EPTC     6  443 .5      Corn                                                                              10 ST           80                                                                              MF                              EPTC     6  444 .5      Corn                                                                              10 ST           65                                                                              MF                              EPTC     6  445 .5      Corn                                                                              70 MF           75                                                                              MF                              EPTC     6  446 .5      Corn                                                                              20 ST           65                                                                              MF                              EPTC     6  447 .5      Corn                                                                              60 MF           80                                                                              MF                              EPTC     6  448 .5      Corn                                                                              30 ST, MF       70                                                                              MF                              EPTC     6  449 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  450 .5      Corn                                                                              60 ST, MF       80                                                                              MF                              EPTC     6  451 .5      Corn                                                                              20 ST           70                                                                              MF                              EPTC     6  452 .5      Corn                                                                              70 ST, MF       80                                                                              MF                              EPTC     6  453 .5      Corn                                                                              20 ST           60                                                                              MF                              EPTC     6  454 .5      Corn                                                                              70 MF           75                                                                              MF                              EPTC     6  455 .5      Corn                                                                              20 ST           65                                                                              MF                              EPTC     6  456 .5      Corn                                                                              60 ST, MF       75                                                                              MF                              EPTC     6  457 .5      Corn                                                                              70 ST, MF       80                                                                              MF                              EPTC     6  458 .5      Corn                                                                              50 ST, MF       70                                                                              MF                              EPTC     6  459 .5      Corn                                                                              40 ST, MF       80                                                                              MF                              EPTC     6  460 .5      Corn                                                                              60 ST, MF       80                                                                              MF                              EPTC     6  461 .5      Corn                                                                              10 ST           80                                                                              MF                              EPTC     6  462 .5      Corn                                                                              30 ST, MF       75                                                                              MF                              EPTC     6  463 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  464 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  465 .5      Corn                                                                              50 ST, MF       80                                                                              MF                              EPTC     6  466 .5      Corn                                                                              20 ST, MF       70                                                                              MF                              EPTC     6  467 .5      Corn                                                                              0               75                                                                              MF                              EPTC     6  468 .5      Corn                                                                              60 ST, MF       80                                                                              MF                              EPTC     6  469 .5      Corn                                                                              10 ST           80                                                                              MF                              EPTC     6  470 .5      Corn                                                                              60 MF           75                                                                              MF                              EPTC     6  471 .5      Corn                                                                              50 ST, MF       65                                                                              MF                              EPTC     6  472 .5      Corn                                                                              20 ST, MF       25                                                                              MF                              EPTC     6  473 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  474 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  475 .5      Corn                                                                              20 ST, MF       70                                                                              MF                              EPTC     6  476 .5      Corn                                                                              10 ST           75                                                                              MF                              EPTC     6  477 .5      Corn                                                                              30 ST, MF       80                                                                              MF                              EPTC     6  478 .5      Corn                                                                              20 ST, MF       80                                                                              MF                              EPTC     6  479 .5      Corn                                                                              60 ST, MF       80                                                                              MF                              EPTC     6  480 .5      Corn                                                                              70 ST, MF       80                                                                              MF                              EPTC     6  481 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  482 .5      Corn                                                                              60 ST, MF       80                                                                              MF                              EPTC     6  483 .5      Corn                                                                              70 ST, MF       80                                                                              MF                              EPTC     6  484 .5      Corn                                                                              60 MF           75                                                                              MF                              EPTC     6  485 .5      Corn                                                                              70 MF           80                                                                              MF                              EPTC     6  486 .5      Corn                                                                              10 ST           25                                                                              MF                              EPTC     6  487 .5      Corn                                                                              10 ST           40                                                                              MF                              EPTC     6  488 .5      Corn                                                                              50 ST, MF       55                                                                              MF                              EPTC     6  489 .5      Corn                                                                              0               0                                 EPTC     6  490 .5      Corn                                                                              10 ST   30 ST   70     70                                                                              MF                       EPTC     6  491 .5      Corn                                                                              20      50 ST, MF                                                                             70     70                                                                              MF                       EPTC     6  492 .5      Corn                                                                              50      75 ST, MF                                                                             80                                                                              MF                              EPTC     6  493 .5      Corn                                                                              40 ST, MF       80                                                                              ST, MF                          EPTC     6  494 .5      Corn                                                                              0       50 ST, MF                                                                             75                                                                              MF   85                                                                              MF                       EPTC     6  495 .5      Corn                                                                              10 ST   0       77                                                                              MF   75                                                                              MF                       EPTC     6  496 .5      Corn                                                                              30 ST, MF                                                                             60 ST, MF                                                                             95                                                                              MF   98                                                                              MF                       EPTC     6  497 .5      Corn                                                                              50 MF           98                                                                              MF                              EPTC     6  498 .5      Corn                                                                              30 ST, MF       97                                                                              MF                              EPTC     6  499 .5      Corn                                                                              60 MF           98                                                                              MF                              EPTC     6  500 .5      Corn                                                                              10 ST   20 ST   78                                                                              MF   97                                                                              MF                       EPTC     6  501 .5      Corn                                                                              10 ST   20 ST   50                                                                              MF   70                         EPTC     6  502 .5      Corn                                                                              100                                                                              IG   100                                                                              IG   55                                                                              MF   60                                                                              MF                       EPTC     6  503 .5      Corn                                                                              100                                                                              IG   100                                                                              IG   30                                                                              MF   40                                                                              MF                       EPTC     6  504 .5      Corn                                                                              0       0       5 MF   30                                                                              MF                       EPTC     6  505 .5      Corn                                                                              30 ST   30 ST   0      0                          EPTC     6  506 .5      Corn                                                                              10 ST   25 MF   58                                                                              MF                              EPTC     6  507 .5      Corn                                                                              20 ST, MF       65                                                                              MF                              EPTC     6  508 .5      Corn                                                                              10 ST           78                                                                              MF                              EPTC     6  509 .5      Corn                                                                              40 ST, MF       89                                                                              MF                              EPTC     6  510 .5      Corn                                                                              0       0       84                                                                              MF   94                         EPTC     6  511 .5      Corn                                                                              100                                                                              IG   100                                                                              IG   45                                                                              MF   50                                                                              MF                       EPTC     6  512 .5      Corn                                                                              100                                                                              IG   100                                                                              IG   0      0                          EPTC     6  513 .5      Corn                                                                              100                                                                              IG   100                                                                              IG   0      0                          EPTC     6  --  --      Corn                                                                              90 MF                                             S-2,3,3-Tri-                                                                           1  6   .25     Wheat                                                                             5  ST                                             chloroallyl                                                                   diisopropyl                                                                   thiolcarbamate                                                                S-2,3,3-Tri-                                                                           1  6   .5      Wheat                                                                             20 ST                                             chloroallyl                                                                   diisopropyl                                                                   thiolcarbamate                                                                S-2,3,3-Tri-                                                                           1  --  --      Wheat                                                                             90 MF                                             chloroallyl                                                                   diisopropyl                                                                   thiolcarbamate                                                                EPTC +   6 +                                                                              6   1.0     Corn                                                                              0       0       0      0                          2-chloro-4-                                                                            1                                                                    ethylamino-6-                                                                 isopropylamino-                                                               s-triazine                                                                    EPTC +   6 +                                                                              6   0.01    Corn                                                                              0       0                                         2-chloro-4-                                                                            1                                                                    ethylamino-6-                                                                 isopropylamino-                                                               s-triazine                                                                    EPTC +   6 +                                                                              6   1.0     Corn                                                                              0       0       0      0                          2-chloro-4,6-                                                                          1                                                                    bis(ethylamino)-                                                              s-triazine                                                                    EPTC +   6 +                                                                              6   0.01    Corn                                                                              0       0                                         2-chloro-4,6-                                                                          1                                                                    bis(ethylamino)-                                                              s-triazine                                                                    EPTC +   6 +                                                                              6   1.0     Corn                                                                              0       0       0      0                          2(4-chloro-6-                                                                          1                                                                    ethylamino-s-                                                                 triazine-2-                                                                   yl-amino)-2-                                                                  methylpropio-                                                                 nitrile                                                                       EPTC +   6 +                                                                              6   0.01    Corn                                                                              0       0                                         2(4-chloro-6-                                                                          1                                                                    ethylamino-s-                                                                 triazine-2-                                                                   yl-amino)-2-                                                                  methylpropio-                                                                 nitrile                                                                       EPTC +   6 +                                                                              6   1.0     Corn                                                                              0       0       0      0                          2-chloro-4-                                                                            1                                                                    cyclopropyl-                                                                  amino-6-iso-                                                                  propylamino-                                                                  s-triazine                                                                    EPTC +   6 +                                                                              6   0.01    Corn                                                                              0       0                                         2-chloro-4-                                                                            1                                                                    cyclopropyl-                                                                  amino-6-iso-                                                                  propylamino-                                                                  s-triazine                                                                    EPTC +   6 +                                                                              6   1.0     Corn                                                                              0       0       0      0                          2,4-D    1                                                                    EPTC +   6 +                                                                              6   0.01    Corn                                                                              0       0                                         2,4-D    1                                                                    S-propyl di-                                                                           6 +                                                                              6   1.0     Corn                                                                              0       0       0      0                          propyl thiol-                                                                          1                                                                    carbamate +                                                                   2-chloro-4-                                                                   ethylamino-6-                                                                 isopropylamino-                                                               s-triazine                                                                    S-propyl di-                                                                           6  --  --      Corn                                                                              90 MF                                             propyl thiol-                                                                 carbamate                                                                     S-propyl di-                                                                           6 +                                                                              6   0.01    Corn                                                                              0       0       0      0                          propyl thiol-                                                                          1                                                                    carbamate +                                                                   2-chloro-4-                                                                   ethylamino-6-                                                                 isopropylamino-                                                               s-triazine                                                                    S-propyl di-                                                                           6 +                                                                              6   1.0     Corn                                                                              0       0       0      0                          propyl thiol-                                                                          1                                                                    carbamate +                                                                   2-chloro-4,6-                                                                 bis(ethylamino)-                                                              s-triazine                                                                    S-propyl di-                                                                           6 +                                                                              6   0.01    Corn                                                                              0       0       0      0                          propyl thiol-                                                                          1                                                                    carbamate +                                                                   2-chloro-4,6-                                                                 bis(ethylamino)-                                                              s-triazine                                                                    S-propyl di-                                                                           6 +                                                                              6   1.0     Corn                                                                              0       0       0      0                          propyl thiol-                                                                          1                                                                    carbamate +                                                                   2(4-chloro-6-                                                                 ethylamino-s-                                                                 triazine-2-yl-                                                                amino)-2-methyl-                                                              propionitrile                                                                 S-propyl di-                                                                           6 +                                                                              6   0.01    Corn                                                                              0       0                                         propyl thiol-                                                                          1                                                                    carbamate +                                                                   2(4-chloro-6-                                                                 ethylamino-2-                                                                 triazine-2-yl-                                                                amino)-2-methyl-                                                              propionitrile                                                                 S-propyl di-                                                                           6 +                                                                              6   1.0     Corn                                                                              0       0       0      0                          propyl thiol-                                                                          1                                                                    carbamate +                                                                   2-chloro-4-                                                                   cyclopropyl-                                                                  amino-6-iso-                                                                  propylamino-                                                                  s-triazine                                                                    S-propyl di-                                                                           6 +                                                                              6   0.01    Corn                                                                              0       0                                         propyl thiol-                                                                          1                                                                    carbamate +                                                                   2-chloro-4-                                                                   cyclopropyl-                                                                  amino-6-iso-                                                                  propylamino-                                                                  s-triazine                                                                    S-propyl di-                                                                           6 +                                                                              6   1.0     Corn                                                                              0       0       0      0                          propyl thiol-                                                                          1                                                                    carbamate +                                                                   2,4-D                                                                         S-propyl di-                                                                           6 +                                                                              6   0.01    Corn                                                                              0       0                                         propyl thiol-                                                                          1                                                                    carbamate +                                                                   2,4-D                                                                         S-propyl di-                                                                           6  6   1.0     Corn                                                                              0       0       0      0                          propyl thiol-                                                                 carbamate                                                                     S-propyl di-                                                                           6  6   0.01    Corn                                                                              0       0                                         propyl thiol-                                                                 carbamate                                                                     S-ethyl diiso-                                                                         8 +                                                                              6   1.0     Corn                                                                              0       0       0      0                          butyl thiol-                                                                           1                                                                    carbamate +                                                                   2-chloro-4-                                                                   ethylamino-6-                                                                 isopropylamino-                                                               s-triazine                                                                    S-ethyl diiso-                                                                         8 +                                                                              6   0.01    Corn                                                                              0       0                                         butyl thiol-                                                                           1                                                                    carbamate +                                                                   2-chloro-4-                                                                   ethylamino-6-                                                                 isopropylamino-                                                               s-triazine                                                                    S-ethyl diiso-                                                                         8 +                                                                              6   1.0     Corn                                                                              0       0       0      0                          butyl thiol-                                                                           1                                                                    carbamate +                                                                   2-chloro-4,6-                                                                 bis(ethylamino)-                                                              s-triazine                                                                    S-ethyl diiso-                                                                         8 +                                                                              6   0.01    Corn                                                                              0       0                                         butyl thiol-                                                                           1                                                                    carbamate +                                                                   2-chloro-4,6-                                                                 bis(ethylamino)-                                                              s-triazine                                                                    S-ethyl diiso-                                                                         8 +                                                                              6   1.0     Corn                                                                              0       0       0      0                          butyl thiol-                                                                           1                                                                    carbamate +                                                                   2(4-chloro-6-                                                                 ethylamino-s-                                                                 triazine-2-yl-                                                                amino)-2-methyl-                                                              propionitrile                                                                 S-ethyl diiso-                                                                         8 +                                                                              6   0.01    Corn                                                                              0       0                                         butyl thiol-                                                                           1                                                                    carbamate +                                                                   2(4-chloro-6-                                                                 ethylamino-s-                                                                 triazine-2-yl-                                                                amino)-2-methyl-                                                              propionitrile                                                                 S-ethyl diiso-                                                                         8 +                                                                              6   1.0     Corn                                                                              0       0       0      0                          butyl thiol-                                                                           1                                                                    carbamate +                                                                   2-chloro-4-                                                                   cyclopropyl-                                                                  amino-6-iso-                                                                  propylamino-                                                                  s-triazine                                                                    S-ethyl diiso-                                                                         8 +                                                                              6   0.01    Corn                                                                              0       0                                         butyl thiol-                                                                           1                                                                    carbamate +                                                                   2-chloro-4-                                                                   cyclopropyl-                                                                  amino-6-iso-                                                                  propylamino-                                                                  s-triazine                                                                    S-ethyl diiso-                                                                         8 +                                                                              6   1.0     Corn                                                                              0       0       0      0                          butyl thiol-                                                                           1                                                                    carbamate +                                                                   2,4-D                                                                         S-ethyl diiso-                                                                         8 +                                                                              6   0.01    Corn                                                                              0       0                                         butyl thiol-                                                                           1                                                                    carbamate +                                                                   2,4-D                                                                         S-ethyl diiso-                                                                         8  6   1.0     Corn                                                                              0       0       0      0                          butyl thiol-                                                                  carbamate                                                                     S-ethyl diiso-                                                                         8  6   0.01    Corn                                                                              0       0       0      0                          butyl thiol-                                                                  carbamate                                                                     S-2,3,3-tri-                                                                           8  6   1.0     Corn                                                                              0       0       0      0                          chloroallyl-                                                                  diisopropyl                                                                   thiolcarbamate                                                                S-2,3,3-tri-                                                                           8  6   0.01    Corn                                                                              0       0       0      0                          chloroallyl-                                                                  diisopropyl                                                                   thiolcarbamate                                                                S-ethyl diiso-                                                                         8  --  --      Corn                                                                              20 MF                                             butyl thiol-                                                                  carbamate                                                                     S-2,3,3-tri-                                                                           8  --  --      Corn                                                                              30 ST                                             chloroallyl-                                                                  diisopropyl                                                                   thiolcarbamate                                                                __________________________________________________________________________     EPTC = Sethyl, dipropylthiocarbamate                                          ST = stunting                                                                 MF = malformation                                                             IG = inhibited germination                                                    LB = leaf burn                                                           

The antidote compounds of the present invention can be used in anyconvenient form. Thus, the antidote compounds can be made intoemulsifiable liquids, emulsifiable concentrates, liquid, wettablepowder, powders, granular or any other convenient form. In its preferredform, the antidote compounds are admixed with the thiolcarbamates andincorporated into the soil prior to or after planting the seed. It is tobe understood, however, that the thiolcarbamate herbicide can beincorporated into the soil and thereafter the antidote compound can beincorporated into the soil. Moreover, the seed can be treated with theantidote compound and planted into the soil which has been treated withherbicides or untreated with the herbicide and subsequently treated withthe herbicide. The method of addition of the antidote compound does notaffect the herbicidal activity of the carbamate compounds.

The amount of antidote composition present can range between about0.0001 to about 30 parts by weight per each part by weight ofthiolcarbamate herbicide. The exact amount of antidote compound willusually be determined on economic ratios for the most effective amountusable.

When used in the claims of this application, the phrase "activeherbicidal compound" is meant to include the active thiolcarbamatesalone or the thiolcarbamates admixed with other active compounds such asthe s-triazines and 2,4-D, or the active acetanilides and the like.Also, the active herbicidal compound is different from the antidotecompound.

It is clear that the classes of herbicidal agents described andillustrated herein are characterized as effective herbicides exhibitingsuch activity. The degree of this herbicidal activity varies amongspecific compounds and among combinations of specific compounds withinthe classes. Similarly, the degree of activity to some extent variesamong the species of plants to which a specific herbicidal compound orcombination may be applied. Thus, selection of a specific herbicidalcompound or combination to control undesirable plant species readily maybe made. Within the present invention the prevention of injury to adesired crop species in the presence of a specific compound orcombination may be achieved. The beneficial plant species which can beprotected by this method is not intended to be limited by the specificcrops employed in the examples.

The herbicidal compounds employed in the method of this invention areactive herbicides of a general type. That is, the members of the classesare herbicidally effective against a wide range of plant species with nodiscrimination between desirable and undesirable species. The method ofcontrolling vegetation comprises applying an herbicidally effectiveamount of the hereindescribed herbicidal compounds to the area or plantlocus where control is desired.

An herbicide as used herein means a compound which controls or modifiesthe growth of vegetation or plants. Such controlling or modifyingeffects include all deviations from natural development; for example,killing, retardation, defoliation, desiccation, regulation, stunting,tillering, stimulation, dwarfing and the like. By "plants" it is meantgerminant seeds, emerging seedlings, and established vegetation,including the roots and above-ground portions.

The herbicides indicated in the tables are used at rates which produceeffective control of undesirable vegetation. The rates are within therecommended amounts set forth by the supplier. Therefore, the weedcontrol in each instance is commercially acceptable within the desiredamount.

In the above description of the antidote compounds, the followingembodiments are intended for the various substituent groups: alkylincludes, unless otherwise provided for, those members which containfrom 1 to 20 carbon atoms, inclusive, in both straight and branchedchain configurations; alkenyl includes unless otherwise provided for,those members which contain at least one olefinic double bond andcontain from 2 to 20 carbon atoms, inclusive, preferably from 2 to 12carbon atoms, inclusive, in both straight and branched chainconfigurations; and alkynyl includes, unless otherwise provided for,those members which contain at least one acetylenic triple bond andcontain from 2 to 20 carbon atoms, inclusive, preferably from 2 to 12carbon atoms, inclusive, in both straight and branched chainconfigurations.

What is claimed is:
 1. A method of controlling weed pests and protectingcorn plants which comprises adding to the habitat thereof anherbicidally effective amount of a composition an active thiolcarbamateherbicide admixed with an active striazine herbicide and anon-phytotoxic antidotally effective amount ofN,N-diallyldichloroacetamide.
 2. A herbicidal composition comprising anactive thiocarbamate herbicide admixed with an active s-triazineherbicide and a non-phytotoxic antidotally effective amount of anantidote having the formula ##STR329## wherein said antidote is presentin an amount ranging between about 0.0001 to 30 parts by weight for eachpart by weight of the thiolcarbamate herbicide.
 3. The herbicidalcomposition as set forth in claim 2 wherein said active thiocarbamate isselected from the group consisting of EPTC, S-ethyl diisobutylthiocarbamate, S-propyl dipropyl thiocarbamate,S-2,3,3-trichloroallyl-di-isopropyl thiocarbamate,S-4-chlorobenzyl-diethyl thiocarbamate, S-ethyl cyclohexylethylthiocarbamate and S-ethyl hexahydro-1H-azepine-1-carbothioate and saidactive striazine herbicide is selected from the group consisting of2-chloro-4-ethylamino-6-isopropylamino-s-triazine,2-chloro-4,6-bis(ethylamino)-s-triazine,2-(4-chloro-6-ethylamino-s-triazine-2-yl-amino)-2-methylpropionitrileand 2-chloro-4-cyclopropylamino-6-isopropylamino-s-triazine.
 4. Theherbicide composition as set forth in claim 2 wherein said activethiocarbamate is EPTC (S-ethyl di-n-propyl thiolcarbamate) and saidactive s-triazine is 2-chloro-4-ethylamino-6-isopropylamino-s-triazine5. The herbicide composition as set forth in claim 2 wherein said activethiolcarbamate is S-ethyl diisobutyl thiolcarbamate and said actives-triazine is 2-chloro-4,-ethylamino-6-isopropylamino-s-triazine.
 6. Theherbicide composition as set forth in claim 2 wherein said activethiocarbamate is S-propyl dipropyl thiocarbamate and said actives-triazine is 2-chloro-4-ethylamino-6-isopropylamino-s-triazine.
 7. Theherbicide composition as set forth in claim 2 wherein said activethiolcarbamate is EPTC (S-ethyl di-n-propyl thiolcarbamate) and saidactive s-triazine is 2-chloro-4,6-bis(ethylamino)-s-triazine.
 8. Theherbicide composition as set forth in claim 2 wherein said activethiolcarbamate is S-ethyl diisobutyl thiolcarbamate and said actives-triazine is 2-chloro-4,6-bis(ethylamino)-s-triazine.
 9. The herbicidecomposition as set forth in claim 2 wherein said active thiolcarbamateis S-propyl dipropyl thiolcarbamate and said active s-triazine is2-chloro-4,6-bis(ethylamino)-s-triazine.
 10. The herbicide compositionas set forth in claim 2 wherein said active thiolcarbamate is EPTC(S-ethyl di-n-propyl thiolcarbamate) and said active s-triazine is2-(4-chloro-6-ethylamino-s-triazine-2-yl-amino)-2-methylpropionitrile.11. The herbicide composition as set forth in claim 2 wherein saidactive thiolcarbamate is S-ethyl diisobutyl thiolcarbamate and saidactive s-triazine is2(4-chloro-6-ethylamino-s-triazine-2-yl-amino-2-methylpropionitrile. 12.The herbicide composition as set forth in claim 2 wherein said activethiocarbamate is S-propyl dipropyl thiolcarbamate and said actives-triazine is2(4-chloro-6-ethylamino-s-triazine-2-yl-amino-2-methylpropionitrile. 13.The herbicide composition as set forth in claim 2 wherein said activethiolcarbamate is EPTC (S-ethyl di-n-propyl thiolcarbamate) and saidactive s-triazine is2-chloro-4-cyclopropylamino-6-isopropylamino-s-triazine.
 14. Theherbicide composition as set forth in claim 2 wherein active s-triazineis 2-chloro-4-cyclopropylamino-6-isopropylamino-a-triazin.
 15. Theherbicide composition as set forth in claim 2 wherein said activethiolcarbamate is S-propyl dipropyl thiocarbamate and said actives-triazine is 2-chloro-4-cycloporpylamino-6-isopropylamino-s-triazin.